Aromatic amine derivative and organic electroluminescent device using same

ABSTRACT

Disclosed is an organic electroluminescence device in which an organic thin film which is composed of one or more layers including at least a light-emitting layer is interposed between a cathode and an anode. Since at least one layer of the organic thin film contains a novel aromatic amine derivative, which has an asymmetric structure wherein two different amine units are bonded through a linking group, by itself or as a component of a mixture, molecules are hardly crystallized, thereby improving the production yield of the organic electroluminescence device. This organic electroluminescence device has a long life.

CROSS-REFERENCE TO RELATED APPLICATIONS

The present application is a continuation of U.S. application Ser. No.13/345,536, filed Jan. 6, 2012; which is a Continuation application ofU.S. application Ser. No. 11/813,377, filed on Jul. 5, 2007, which is a35 U.S.C. §371 National Stage patent application of International patentapplication PCT/JP2005/023368, filed on Dec. 20, 2005, which claimspriority to Japanese patent application JP 2005-001008, filed on Jan. 5,2005, all of which are incorporated herein by reference.

TECHNICAL FIELD

The present invention relates to aromatic amine derivatives and anorganic electroluminescence (EL) device using any one of them, inparticular, an organic EL device in which a molecule hardlycrystallizes, which is produced with improved yields, and which has along lifetime and an aromatic amine derivative realizing the organic ELdevice.

BACKGROUND ART

An organic EL device is a spontaneous light emitting device whichutilizes the principle that a fluorescent substance emits light byenergy of recombination of holes injected from an anode and electronsinjected from a cathode when an electric field is applied. Since anorganic EL device of the laminate type driven under a low electricvoltage was reported by C. W. Tang et al. of Eastman Kodak Company (C.W. Tang and S. A. Vanslyke, Applied Physics Letters, Volume 51, Pages913, 1987 or the like), many studies have been conducted on organic ELdevices using organic materials as the constituent materials. Tang etal. used tris(8-quinolinolato)aluminum for a light emitting layer and atriphenyldiamine derivative for a hole transporting layer. Advantages ofthe laminate structure are that the efficiency of hole injection intothe light emitting layer can be increased, that the efficiency offorming exciton which are formed by blocking and recombining electronsinjected from the cathode can be increased, and that exciton formedwithin the light emitting layer can be enclosed. As described above, forthe structure of the organic EL device, a two-layered structure having ahole transporting (injecting) layer and an electron-transporting lightemitting layer and a three-layered structure having a hole transporting(injecting) layer, a light emitting layer, and an electron-transporting(injecting) layer are well known. To increase the efficiency ofrecombination of injected holes and electrons in the devices of thelaminate type, the structure of the device and the process for formingthe device have been studied.

In general, when an organic EL device is driven or stored in anenvironment of a high temperature, adverse effects such as a change inthe luminescent color, a decrease in emission efficiency, an increase inthe voltage for driving, and a decrease in the lifetime of lightemission arise. To prevent the adverse effects, it has been necessarythat the glass transition temperature (Tg) of the hole transportingmaterial be elevated. Therefore, it is necessary that the many aromaticgroups be held within the molecule of the hole transporting material,for example, the aromatic diamine derivative in Patent Document 1 andthe fused aromatic ring diamine derivative in Patent Document 2, and ingeneral, a structure having 8 to 12 benzene rings may preferably beused.

However, when a large number of aromatic groups are present in amolecule, crystallization is apt to occur upon production of an organicEL device through the formation of a thin film by using those holetransporting materials. As a result, there arises a problem such as theclogging of the outlet of a crucible to be used in vapor deposition or areduction in yields of the organic EL device due to the generation of afault of the thin film resulting from the crystallization. In addition,a compound having a large number of aromatic groups in any one of itsmolecules generally has a high glass transition temperature (Tg), buthas a high sublimation temperature. Accordingly, there arises a problemin that the lifetime of the compound is short because a phenomenon suchas decomposition at the time of vapor deposition or the formation of anonuniform deposition film is expected to occur.

Meanwhile, there is a known document disclosing an asymmetric aromaticamine derivative. For example, Patent Document 3 describes an aromaticamine derivative having an asymmetric structure. However, the documenthas no specific example, and has no description concerningcharacteristics of anasymmetric compound. In addition, Patent Document 4describes an asymmetric aromatic amine derivative having phenanthrene asan example. However, the derivative is treated in the same way as thatof a symmetric compound, and the document has no description concerningcharacteristics of an asymmetric compound. In addition, none of thosepatents explicitly describes a method of producing an asymmetriccompound in spite of the fact that the asymmetric compound requires aspecial synthesis method. Further, Patent Document 5 describes a methodof producing an aromatic amine derivative having an asymmetricstructure, but has no description concerning characteristics of anasymmetric compound. Patent Document 6 describes an asymmetric compoundwhich has a high glass transition temperature and which is thermallystable, but exemplifies only a compound having carbazole. In addition,the inventors of the present invention have produced a device by usingthe compound. As a result, they have found that a problem lies in theshort lifetime of the device.

As described above, an organic EL device having a long lifetime has beenreported, but it cannot be said yet that the device always showssufficient performance. In view of the foregoing, the development of anorganic EL device having further excellent performance has been stronglydesired.

-   [Patent Document 1] U.S. Pat. No. 4,720,432-   [Patent Document 2] U.S. Pat. No. 5,061,569-   [Patent Document 3] JP-A-08-48656-   [Patent Document 4] JP-A-11-135261-   [Patent Document 5] JP-A-2003-171366-   [Patent Document 6] U.S. Pat. No. 6,242,115

DISCLOSURE OF THE INVENTION Problems to be Solved by the Invention

The present invention has been made with a view to solving theabove-mentioned problems, and an object of the present invention is toprovide an organic EL device, in which a molecule hardly crystallizes,which can be produced with improved yields, and which has a longlifetime, and an aromatic amine derivative realizing the organic ELdevice.

Means for Solving the Problems

The inventors of the present invention have made extensive studies witha view to achieving the above-mentioned object. As a result, they havefound that the use of a novel aromatic amine derivative having anasymmetric structure in which two different amine units are bondedthrough a linking group as represented by the following general formula(1) as a material for an organic EL device, in particular, a holetransporting material can solve the above-mentioned problems. Thus, theyhave completed the present invention.

In addition, the inventors of the present invention have found that anamino group substituted by an aryl group is suitable as an asymmetricamine unit. An interaction between molecules of the amine unit is smallbecause the unit has steric hindrance. Accordingly, the unit has effectssuch that: crystallization is suppressed; yield in which an organic ELdevice is produced is improved; decomposition of a molecule issuppressed at the time of vapor deposition because it is possible todeposit at a low sublimation temperature; and an organic EL devicehaving a long lifetime can be provided. It has been found that theasymmetric amine unit can provide an organic EL device having asignificantly long lifetime, in particular, when the amine unit iscombined with a blue light emitting device.

That is, the present invention provides anaromatic amine derivativerepresented by the following general formula (1):

A-L-B  (1)

where:

L represents a linking group composed of a substituted or unsubstitutedarylene group having 5 to 50 ring atoms, or a linking group obtained bybonding multiple substituted or unsubstituted arylene groups each having5 to 50 ring atoms through a single bond, an oxygen atom, a sulfur atom,a nitrogen atom, or a saturated or unsaturated, divalent aliphatichydrocarbon group having 1 to 20 ring carbon atoms;

A represents a diarylamino group represented by the following generalformula (2); and

B represents a diarylamino group represented by the following generalformula (3) provided that A and B are not identical to each other:

where Ar₁ to Ar₄ each independently represent a substituted orunsubstituted aryl group having 5 to 50 ring atoms provided that threeor more of Ar₁ to Ar₄ represent aryl groups different from one another.

The present invention provides an aromatic amine derivative representedby the general formula (1), in which all four of Ar₁ to Ar₄ in thegeneral formulae (2) and (3) represent aryl groups different from oneanother.

The present invention provides an aromatic amine derivative representedby the general formula (1), in which Ar₃ and Ar₄ in the general formula(3) each independently represent a group represented by the followinggeneral formula (4):

where Ar₅ represents a substituted or unsubstituted aryl group having 5to 50 ring atoms, and m represents an integer of 1 to 5.

The present invention provides an aromatic amine derivative representedby the general formula (1), in which Ar₃ and Ar₄ in the general formula(3) each independently represent a group represented by the followinggeneral formula (5):

where Ar₆ represents a substituted or unsubstituted aryl group having 5to 50 ring atoms.

The present invention provides an aromatic amine derivative representedby the general formula (1), in which Ar₁ represents a substituted orunsubstituted naphthyl group, and Ar₃ and Ar₄ each independentlyrepresent a group represented by the general formula (5).

The present invention provides an aromatic amine derivative representedby the general formula (1), in which Ar₂ in the general formula (2) andAr₄ in the general formula (3) each independently represent a grouprepresented by the following general formula (4):

where Ar₅ represents a substituted or unsubstituted aryl group having 5to 50 ring atoms, and m represents an integer of 1 to 5.

The present invention provides an aromatic amine derivative representedby the general formula (1), in which Ar₂ in the general formula (2) andAr₄ in the general formula (3) each independently represent a grouprepresented by the following general formula (5):

where Ar₆ represents a substituted or unsubstituted aryl group having 5to 50 ring atoms.

The present invention provides an aromatic amine derivative representedby the general formula (1), in which Ar₁ represents a substituted orunsubstituted fused ring group having 11 to 50 ring atoms, and Ar₃ andAr₄, or Ar₂ and Ar₄ each independently represent a group represented bythe above-mentioned general formula (4) or (5).

The present invention provides an aromatic amine derivative representedby the general formula (1), in which Ar₁ and Ar₃ each independentlyrepresent a substituted or unsubstituted fused ring group having 10 to50 ring atoms.

The present invention provides an aromatic amine derivative representedby the general formula (1), in which Ar₁ and Ar₂ each independentlyrepresent a substituted or unsubstituted fused ring group having 10 to50 ring atoms.

The present invention provides an aromatic amine derivative representedby the general formula (1), in which Ar₃ and Ar₄ are identical to eachother, and Ar₃ and Ar₄, or Ar₂ and Ar₄ each independently represent agroup represented by the above-mentioned general formula (4) or (5), orAr₁ alone represents, or Ar₁ and Ar₃ each represent, a fused ring.

The present invention provides an aromatic amine derivative representedby the general formula (1), in which Ar₂ and Ar₃ are identical to eachother, and Ar₃ and Ar₄, or Ar₂ and Ar₄ each independently represent agroup represented by the above-mentioned general formula (4) or (5), orAr₁ alone represents, or Ar₁ and Ar₃ each represent, a fused ring.

The present invention provides an aromatic amine derivative representedby the general formula (1), in which a total number of the ring atoms ofthe aryl groups represented by Ar₁ to Ar₄ is 41 to 96.

The present invention provides an aromatic amine derivative representedby the general formula (1), in which a total number of the ring atoms ofthe aryl groups represented by Ar₁ to Ar₄ is 45 to 72.

The present invention provides any one of the aromatic amine derivativeas described above, which is a material for an organicelectroluminescence device.

The present invention provides any one of the aromatic amine derivativesas described above, which is a hole transporting material for an organicelectroluminescence device.

The present invention provides an organic electroluminescence deviceincluding an organic thin film layer composed of one or more layersincluding at least a light emitting layer, the organic thin film layerbeing interposed between a cathode and an anode in which at least onelayer of the organic thin film layer contains any one of the aromaticamine derivatives as described above alone or as a component of amixture.

The present invention provides the organic electroluminescence device asdescribed above, in which the organic thin film layer has a holetransporting layer, and the hole transporting layer contains any one ofthe aromatic amine derivatives alone or as a component of a mixture.

The present invention provides the organic electroluminescence device asdescried above, in which the light emitting layer contains an arylaminecompound and/or a styrylamine compound.

Further, the present invention provides any one of the organicelectroluminescence devices as described above which emits bluish light.

Effect of the Invention

An aromatic amine and an organic EL device using the aromatic aminederivative of the present invention, which hardly cause thecrystallization of a molecule, can improve yields upon production of theorganic EL device, and can increase the lifetime of the organic ELdevice.

BEST MODE FOR CARRYING OUT THE INVENTION

An aromatic amine derivative of the present invention is represented bythe following general formula (1).

A-L-B  (1)

In the general formula (1), L represents (I) a linking group composed ofa substituted or unsubstituted arylene group having 5 to 50 ring atoms,or (II) a linking group obtained by bonding multiple substituted orunsubstituted arylene groups each having to 50 ring atoms through (II-1)a single bond, (II-2) an oxygen atom (—O—), (II-3) a sulfur atom (—S—),(II-4) a nitrogen atom (—NH— or —NR— [where R represents asubstituent]), or (II-5) a saturated or unsaturated, divalent aliphatichydrocarbon group having 1 to 20 ring carbon atoms.

Examples of the arylene group having 5 to 50 ring atoms in each of theabove-mentioned items (I) and (II) include a 1,4-phenylene group, a1,2-phenylene group, a 1,3-phenylene group, a 1,4-naphthylene group, a2,6-naphthylene group, a 1,5-naphthylene group, a 9,10-anthranylenegroup, a 9,10-phenanthrenylene group, a 3,6-phenanthrenylene group, a1,6-pyrenylene group, a 2,7-pyrenylene group, a 6,12-chrysenylene group,a 1,1′-biphenylene group, a 4,4′-biphenylene group, a 3,3′-biphenylenegroup, a 2,2′-biphenylene group, a 2,7-fluorenylene group, a2,5-thiophenylene group, a 2,5-silolylene group, a 2,5-oxadiazolylenegroup, and a terphenylene group. Of those, a 1,4-phenylene group, a1,2-phenylene group, a 1,3-phenylene group, a 1,4-naphthylene group, a9,10-anthranylene group, a 6,12-chrysenylene group, a 4,4′-biphenylenegroup, a 3,3′-biphenylene group, a 2,2′-biphenylene group, and a2,7-fluorenylene group are preferable.

The saturated or unsaturated, divalent aliphatic hydrocarbon grouphaving 1 to 20 ring carbon atoms in the above-mentioned item (II-5) maybe linear, branched, or cyclic, and examples of the group include amethylene group, an ethylene group, a propylene group, an isopropylenegroup, an ethylidene group, a cyclohexylidene group, and an adamantylenegroup.

L preferably represents a phenylene group, a biphenylene group, aterphenylene group, or a fluorenylene group, more preferably representsa biphenylene group, or particularly preferably represents a1,1′-biphenylene group.

In the general formula (1), A represents a diarylamino group representedby the following general formula (2).

In the general formula (1), B represents a diarylamino group representedby the following general formula (3).

It should be noted that A and B in the general formula (1) are notidentical to each other.

In the general formulae (2) and (3), Ar₁ to Ar₄ each independentlyrepresent a substituted or unsubstituted aryl group having 5 to 50 ringatoms.

Examples of the aryl groups of Ar₁ to Ar₄ include a phenyl group, a1-naphthyl group, a 2-naphthyl group, a 1-anthryl group, a 2-anthrylgroup, a 9-anthryl group, a 1-phenanthryl group, a 2-phenanthryl group,a 3-phenanthryl group, a 4-phenanthryl group, a 9-phenanthryl group, a1-naphthacenyl group, a 2-naphthacenyl group, a 9-naphthacenyl group, a1-pyrenyl group, a 2-pyrenyl group, a 4-pyrenyl group, a 2-biphenylylgroup, a 3-biphenylyl group, a 4-biphenylyl group, a p-terphenyl-4-ylgroup, a p-terphenyl-3-yl group, a p-terphenyl-2-yl group, anm-terphenyl-4-yl group, an m-terphenyl-3-yl group, an m-terphenyl-2-ylgroup, an o-tolyl group, an m-tolyl group, a p-tolyl group, ap-t-butylphenyl group, a p-(2-phenylpropyl)phenyl group, a3-methyl-2-naphthyl group, a 4-methyl-1-naphthyl group, a4-methyl-1-anthryl group, a 4′-methylbiphenylyl group, a4″-t-butyl-p-terphenyl-4-yl group, a fluoranthenyl group, a fluorenylgroup, a 1-pyrrolyl group, a 2-pyrrolyl group, a 3-pyrrolyl group, apyrazinyl group, a 2-pyridinyl group, a 3-pyridinyl group, a 4-pyridinylgroup, a 1-indolyl group, a 2-indolyl group, a 3-indolyl group, a4-indolyl group, a 5-indolyl group, a 6-indolyl group, a 7-indolylgroup, a 1-isoindolyl group, a 2-isoindolyl group, a 3-isoindolyl group,a 4-isoindolyl group, a 5-isoindolyl group, a 6-isoindolyl group, a7-isoindolyl group, a 2-furyl group, a 3-furyl group, a 2-benzofuranylgroup, a 3-benzofuranyl group, a 4-benzofuranyl group, a 5-benzofuranylgroup, a 6-benzofuranyl group, a 7-benzofuranyl group, a1-isobenzofuranyl group, a 3-isobenzofuranyl group, a 4-isobenzofuranylgroup, a 5-isobenzofuranyl group, a 6-isobenzofuranyl group, a7-isobenzofuranyl group, a quinolyl group, a 3-quinolyl group, a4-quinolyl group, a 5-quinolyl group, a 6-quinolyl group, a 7-quinolylgroup, an 8-quinolyl group, a 1-isoquinolyl group, a 3-isoquinolylgroup, a 4-isoquinolyl group, a 5-isoquinolyl group, a 6-isoquinolylgroup, a 7-isoquinolyl group, an 8-isoquinolyl group, a 2-quinoxalinylgroup, a 5-quinoxalinyl group, a 6-quinoxalinyl group, a 1-carbazolylgroup, a 2-carbazolyl group, a 3-carbazolyl group, a 4-carbazolyl group,a 9-carbazolyl group, a 1-phenanthridinyl group, a 2-phenanthridinylgroup, a 3-phenanthridinyl group, a 4-phenanthridinyl group, a6-phenanthridinyl group, a 7-phenanthridinyl group, an 8-phenanthridinylgroup, a 9-phenanthridinyl group, a 10-phenanthridinyl group, a1-acridinyl group, a 2-acridinyl group, a 3-acridinyl group, a4-acridinyl group, a 9-acridinyl group, a 1,7-phenanthrolin-2-yl group,a 1,7-phenanthrolin-3-yl group, a 1,7-phenanthrolin-4-yl group, a1,7-phenanthrolin-5-yl group, a 1,7-phenanthrolin-6-yl group, a1,7-phenanthrolin-8-yl group, a 1,7-phenanthrolin-9-yl group, a1,7-phenanthrolin-10-yl group, a 1,8-phenanthrolin-2-yl group, a1,8-phenanthrolin-3-yl group, a 1,8-phenanthrolin-4-yl group, a1,8-phenanthrolin-5-yl group, a 1,8-phenanthrolin-6-yl group, a1,8-phenanthrolin-7-yl group, a 1,8-phenanthrolin-9-yl group, a1,8-phenanthrolin-10-yl group, a 1,9-phenanthrolin-2-yl group, a1,9-phenanthrolin-3-yl group, a 1,9-phenanthrolin-4-yl group, a1,9-phenanthrolin-5-yl group, a 1,9-phenanthrolin-6-yl group, a1,9-phenanthrolin-7-yl group, a 1,9-phenanthrolin-8-yl group, a1,9-phenanthrolin-10-yl group, a 1,10-phenanthrolin-2-yl group, a1,10-phenanthrolin-3-yl group, a 1,10-phenanthrolin-4-yl group, a1,10-phenanthrolin-5-yl group, a 2,9-phenanthrolin-1-yl group, a2,9-phenanthrolin-3-yl group, a 2,9-phenanthrolin-4-yl group, a2,9-phenanthrolin-5-yl group, a 2,9-phenanthrolin-6-yl group, a2,9-phenanthrolin-7-yl group, a 2,9-phenanthrolin-8-yl group, a2,9-phenanthrolin-10-yl group, a 2,8-phenanthrolin-1-yl group, a2,8-phenanthrolin-3-yl group, a 2,8-phenanthrolin-4-yl group, a2,8-phenanthrolin-5-yl group, a 2,8-phenanthrolin-6-yl group, a2,8-phenanthrolin-7-yl group, a 2,8-phenanthrolin-9-yl group, a2,8-phenanthrolin-10-yl group, a 2,7-phenanthrolin-1-yl group, a2,7-phenanthrolin-3-yl group, a 2,7-phenanthrolin-4-yl group, a2,7-phenanthrolin-5-yl group, a 2,7-phenanthrolin-6-yl group, a2,7-phenanthrolin-8-yl group, a 2,7-phenanthrolin-9-yl group, a2,7-phenanthrolin-10-yl group, a 1-phenazinyl group, a 2-phenazinylgroup, a 1-phenothiazinyl group, a 2-phenothiazinyl group, a3-phenothiazinyl group, a 4-phenothiazinyl group, a 10-phenothiazinylgroup, a 1-phenoxazinyl group, a 2-phenoxazinyl group, a 3-phenoxazinylgroup, a 4-phenoxazinyl group, a 10-phenoxazinyl group, a 2-oxazolylgroup, a 4-oxazolyl group, a 5-oxazolyl group, a 2-oxadiazolyl group, a5-oxadiazolyl group, a 3-furazanyl group, a 2-thienyl group, a 3-thienylgroup, a 2-methylpyrrol-1-yl group, a 2-methylpyrrol-3-yl group, a2-methylpyrrol-4-yl group, a 2-methylpyrrol-5-yl group, a3-methylpyrrol-1-yl group, a 3-methylpyrrol-2-yl group, a3-methylpyrrol-4-yl group, a 3-methylpyrrol-5-yl group, a2-t-butylpyrrol-4-yl group, a 3-(2-phenylpropyl) pyrrol-1-yl group, a2-methyl-1-indolyl group, a 4-methyl-1-indolyl group, a2-methyl-3-indolyl group, a 4-methyl-3-indolyl group, a2-t-butyl-1-indolyl group, a 4-t-butyl-1-indolyl group, a2-t-butyl-3-indolyl group, and a 4-t-butyl-3-indolyl group.

Of those, a phenyl group, a naphthyl group, a biphenyl group, ananthranyl group, a phenanthryl group, a pyrenyl group, a chrysenylgroup, a fluoranthenyl group, and a fluorenyl group are preferable.

The aromatic amine derivative of the present invention is preferablysuch that Ar₁ to Ar₄ in the general formulae (1) to (3) represent groupsdifferent from one another.

The aromatic amine derivative of the present invention is preferablysuch that at least two of Ar₂ to Ar₄ in the general formulae (1) to (3)each represent an aryl group represented by the following generalformula (4), and is more preferably such that at least two of them eachrepresent an aryl group represented by the following general formula(5):

where Ar₅ represents a substituted or unsubstituted aryl group having 5to 50 ring atoms, examples of the aryl group include the same examplesas those described for the aryl group represented by any one of Ar₁ toAr₄, and m represents an integer of 1 to 5;

where Ar₆ represents a substituted or unsubstituted aryl group having 5to 50 ring atoms.

Examples of a substituent for each of Ar₁ to Ar₆ and L include asubstituted or unsubstituted aryl group having 5 to 50 ring atoms, asubstituted or unsubstituted alkyl group having 1 to 50 carbon atoms, asubstituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, asubstituted or unsubstituted aralkyl group having 1 to 50 carbon atoms,a substituted or unsubstituted aryloxy group having 5 to 50 ring atoms,a substituted or unsubstituted arylthio group having 5 to 50 ring atoms,a substituted or unsubstituted alkoxycarbonyl group having 1 to 50carbon atoms, an amino group substituted by a substituted orunsubstituted aryl group having 5 to 50 ring atoms, a halogen atom, acyano group, a nitro group, a hydroxyl group, and a carboxyl group.

The substituted or unsubstituted aryl group having 5 to 50 ring atoms,which is a substituent for each of Ar₁ to Ar₆ and L includes the sameexamples as those described for the above-mentioned Ar₁ to Ar₆.

Examples of the substituted or unsubstituted alkyl group having 1 to 50carbon atoms, which is a substituent for each of Ar₁ to Ar₆ and Linclude a methyl group, an ethyl group, a propyl group, an isopropylgroup, an n-butyl group, an s-butyl group, an isobutyl group, a t-butylgroup, an n-pentyl group, an n-hexyl group, an n-heptyl group, ann-octyl group, a hydroxymethyl group, a 1-hydroxyethyl group, a2-hydroxyethyl group, a 2-hydroxyisobutyl group, a 1,2-dihydroxyethylgroup, a 1,3-dihydroxyisopropyl group, a 1,3-dihydroxy-2-methyl-2-propylgroup, a 1,2,3-trihydroxypropyl group, a chloromethyl group, a1-chloroethyl group, a 2-chloroethyl group, a 2-chloroisobutyl group, a1,2-dichloroethyl group, a 1,3-dichloroisopropyl group, a1,3-dichloro-2-methyl-2-propyl group, a 1,2,3-trichloropropyl group, abromomethyl group, a 1-bromoethyl group, a 2-bromoethyl group, a2-bromoisobutyl group, a 1,2-dibromoethyl group, a 1,3-dibromoisopropylgroup, a 1,3-dibromo-2-methyl-2-propyl group, a 1,2,3-tribromopropylgroup, an iodomethyl group, a 1-iodoethyl group, a 2-iodoethyl group, a2-iodoisobutyl group, a 1,2-diiodoethyl group, a 1,3-diiodoisopropylgroup, a 1,3-diiodo-2-methyl-2-propyl group, a 1,2,3-triiodopropylgroup, an aminomethyl group, a 1-aminoethyl group, a 2-aminoethyl group,a 2-aminoisobutyl group, a 1,2-diaminoethyl group, a1,3-diaminoisopropyl group, a 1,3-diamino-2-methyl-2-propyl group, a1,2,3-triaminopropyl group, a cyanomethyl group, a 1-cyanoethyl group, a2-cyanoethyl group, a 2-cyanoisobutyl group, a 1,2-dicyanoethyl group, a1,3-dicyanoisopropyl group, a 1,3-dicyano-2-methyl-2-propyl group, a1,2,3-tricyanopropyl group, a nitromethyl group, a 1-nitroethyl group, a2-nitroethyl group, a 2-nitroisobutyl group, a 1,2-dinitroethyl group, a1,3-dinitroisopropyl group, a 1,3-dinitro-2-methyl-2-propyl group, a1,2,3-trinitropropyl group, a cyclopropyl group, a cyclobutyl group, acyclopentyl group, a cyclohexyl group, a 4-methylcyclohexyl group, a1-adamantyl group, a 2-adamantyl group, a 1-norbornyl group, and a2-norbornyl group.

The substituted or unsubstituted alkoxy group having 1 to 50 carbonatoms, which is a substituent for each of Ar₁ to Ar₆ and L isrepresented by —OY, and examples of Y include the same examples as thosedescribed for the above-mentioned alkyl group.

Examples of the substituted or unsubstituted aralkyl group having 6 to50 ring atoms, which is a substituent for each of Ar₁ to Ar₆ and Linclude a benzyl group, a 1-phenylethyl group, a 2-phenylethyl group, a1-phenylisopropyl group, a 2-phenylisopropyl group, a phenyl-t-butylgroup, an α-naphthylmethyl group, a 1-α-naphthylethyl group, a2-α-naphthylethyl group, a 1-α-naphthylisopropyl group, a2-α-naphthylisopropyl group, a β-naphthylmethyl group, a1-β-naphthylethyl group, a 2-β-naphthylethyl group, a1-β-naphthylisopropyl group, a 2-β-naphthylisopropyl group, a1-pyrrolylmethyl group, a 2-(1-pyrrolyl)ethyl group, a p-methylbenzylgroup, an m-methylbenzyl group, an o-methylbenzyl group, ap-chlorobenzyl group, an m-chlorobenzyl group, an o-chlorobenzyl group,a p-bromobenzyl group, an m-bromobenzyl group, a no-bromobenzyl group, ap-iodobenzyl group, an m-iodobenzyl group, an o-iodobenzyl group, ap-hydroxybenzyl group, an m-hydroxybenzyl group, an o-hydroxybenzylgroup, a p-aminobenzyl group, an m-aminobenzyl group, an o-aminobenzylgroup, a p-nitrobenzyl group, an m-nitrobenzyl group, an o-nitrobenzylgroup, a p-cyanobenzyl group, an m-cyanobenzyl group, an o-cyanobenzylgroup, a 1-hydroxy-2-phenylisopropyl group, and a1-chloro-2-phenylisopropyl group.

The substituted or unsubstituted aryloxy group having 5 to 50 ring atomsas a substituent for each of Ar₁ to Ar₆ and L is represented by —OY′,and examples of Y′ include the same examples as those described for thearyl group represented by any one of Ar₁ to Ar₄.

The substituted or unsubstituted arylthio group having 5 to 50 ringatoms as a substituent for each of Ar₁ to Ar₆ and L is represented by—SY', and examples of Y′ include the same examples as those describedfor the aryl group represented by any one of Ar₁ to Ar₄.

The substituted or unsubstituted alkoxycarbonyl group having 1 to 50carbon atoms as a substituent for each of Ar₁ to Ar₆ and L is a grouprepresented by —COOY, and examples of Y include the same examples asthose described for the alkyl group.

Examples of a substituted or unsubstituted aryl group having 5 to 50ring atoms in the amino group substituted by the aryl group as asubstituent for each of Ar₁ to Ar₆ and L include the same examples asthose described for the aryl group represented by any one of Ar₁ to Ar₄.

Examples of the halogen atom as a substituent for each of Ar₁ to Ar₆ andL include a fluorine atom, a chlorine atom, a bromine atom, and aniodine atom.

The aromatic amine derivative of the present invention is preferably amaterial for an organic EL device, and more preferably a holetransporting material for an organic EL device.

Specific examples of the aromatic amine derivative represented by thegeneral formula (1) of the present invention are shown below. However,the present invention is not limited to these exemplified compounds.

Next, the organic EL device of the present invention will be described.

An organic EL device of the present invention includes one or multipleorganic thin film layers including at least a light emitting layer, theone or multiple organic thin film layers being interposed between acathode and an anode, in which at least one layer of the one or moremultiple organic thin film layers contains the aromatic amine derivativealone or as a component of a mixture.

In the organic EL device of the present invention, it is preferablethat: the one or multiple organic thin film layers have a holetransporting layer; and the hole transporting layer contain the aromaticamine derivative of the present invention alone or as a component of amixture. It is more preferable that the hole transporting layer containthe aromatic amine derivative of the present invention as a maincomponent.

The aromatic amine derivative of the present invention is particularlypreferably used in an organic EL device that emits blue-based light.

In addition, in the organic EL device of the present invention, thelight emitting layer preferably contains an aryl amine compound and/or astyrylamine compound.

Examples of the arylamine compound include compounds each represented bythe following general formula (A), and examples of the styrylaminecompound include compounds each represented by the following generalformula (B).

In the general formula (A), Ar₈ represents a group selected from phenyl,biphenyl, terphenyl, stilbene, and distyrylaryl groups, Ar₉ and Ar₁₀each represent a hydrogen atom or an aromatic group having 6 to 20carbon atoms, each of Ar₉ and Ar₁₀ may be substituted, p′ represents aninteger of 1 to 4, and Ar₉ and/or Ar₁₀ are/is more preferablysubstituted by a styryl group.

Here, the aromatic group having 6 to 20 carbon atoms is preferably aphenyl group, a naphthyl group, an anthranyl group, a phenanthryl group,a terphenyl group, or the like.

In the general formula (B), Ar₁₁ to Ar₁₃ each represent an aryl groupwhich has 5 to 40 ring carbon atoms and which may be substituted, and q′represents an integer of 1 to 4.

Here, examples of the aryl group having 5 to 40 ring atoms preferablyinclude phenyl, naphthyl, anthranyl, phenanthryl, pyrenyl, coronyl,biphenyl, terphenyl, pyrrolyl, furanyl, thiophenyl, benzothiophenyl,oxadiazolyl, diphenylanthranyl, indolyl, carbazolyl, pyridyl,benzoquinolyl, fluoranthenyl, acenaphthofluoranthenyl, and stilbene. Inaddition, the aryl group having 5 to 40 ring atoms may further besubstituted by a substituent. Examples of the substituent preferablyinclude: an alkyl group having 1 to 6 carbon atoms such as an ethylgroup, a methyl group, an isopropyl group, an n-propyl group, an s-butylgroup, a t-butyl group, a pentyl group, a hexyl group, a cyclopentylgroup, or a cyclohexyl group; an alkoxy group having 1 to 6 carbon atomssuch as an ethoxy group, a methoxy group, an isopropoxy group, ann-propoxy group, an s-butoxy group, a t-butoxy group, a pentoxy group, ahexyloxy group, a cyclopentoxy group, or a cyclohexyloxy group; an arylgroup having 5 to 40 ring atoms; an amino group substituted by an arylgroup having 5 to 40 ring atoms; an ester group containing an aryl grouphaving 5 to 40 ring atoms; an ester group containing an alkyl grouphaving 1 to 6 carbon atoms; a cyano group; a nitro group; and a halogenatom such as chlorine, bromine, or iodine.

The structure of the organic EL device of the present invention will bedescribed in the following.

(1) Organic El Device Structure

Typical examples of the structure of the organic EL device of thepresent invention include the following:

(1) an anode/light emitting layer/cathode;

(2) an anode/hole injecting layer/light emitting layer/cathode;

(3) an anode/light emitting layer/electron injecting layer/cathode;

(4) an anode/hole injecting layer/light emitting layer/electroninjecting layer/cathode;

(5) an anode/organic semiconductor layer/light emitting layer/cathode;

(6) an anode/organic semiconductor layer/electron barrier layer/lightemitting layer/cathode;

(7) an anode/organic semiconductor layer/light emitting layer/adhesionimproving layer/cathode;

(8) an anode/hole injecting layer/hole transporting layer/light emittinglayer/electron injecting layer/cathode;

(9) an anode/insulating layer/light emitting layer/insulatinglayer/cathode;

(10) an anode/inorganic semiconductor layer/insulating layer/lightemitting layer/insulating layer/cathode;

(11) an anode/organic semiconductor layer/insulating layer/lightemitting layer/insulating layer/cathode;

(12) an anode/insulating layer/hole injecting layer/hole transportinglayer/light emitting layer/insulating layer/cathode; and

(13) an anode/insulating layer/hole injecting layer/hole transportinglayer/light emitting layer/electron injecting layer/cathode.

Of those, the structure (8) is preferably used in ordinary cases.However, the structure is not limited to the foregoing.

The aromatic amine derivative of the present invention may be used inany one of the organic thin film layers of the organic EL device. Thederivative can be used in a light emitting zone or a hole transportingzone. The derivative is used preferably in the hole transporting zone,or particularly preferably in a hole transporting layer, thereby makinga molecule hardly crystallize and improving yields upon production ofthe organic EL device.

The amount of the aromatic amine derivative of the present invention tobe incorporated into the organic thin film layers is preferably 30 to100 mol %.

(2) Transparent Substrate

The organic EL device of the present invention is prepared on atransparent substrate. Here, the transparent substrate is the substratewhich supports the organic EL device. It is preferable that thetransparent substrate have a transmittance of light of 50% or greater inthe visible region of 400 to 700 nm and be flat and smooth.

Examples of the transparent substrate include glass plates and polymerplates. Specific examples of the glass plate include plates made ofsoda-lime glass, glass containing barium and strontium, lead glass,aluminosilicate glass, borosilicate glass, barium borosilicate glass,and quartz. Specific examples of the polymer plate include plates madeof polycarbonate resins, acrylic resins, polyethylene terephthalate,polyether sulfide, and polysulfone.

(3) Anode

The anode in the organic EL device of the present invention has thefunction of injecting holes into the hole transporting layer or thelight emitting layer. It is effective that the anode has a work functionof 4.5 eV or greater. Specific examples of the material for the anodeused in the present invention include indium tin oxide (ITO) alloys, tinoxide (NESA), indium zinc oxide (IZO), gold, silver, platinum, andcopper.

The anode can be prepared by forming a thin film of the electrodematerial described above in accordance with a process such as the vapordeposition process and the sputtering process.

When the light emitted from the light emitting layer is obtained throughthe anode, it is preferable that the anode have a transmittance of theemitted light greater than 10%. It is also preferable that the sheetresistivity of the anode be several hundred Ω/□ or smaller. Thethickness of the anode is, in general, selected in the range of 10 nm to1 μm and preferably in the range of 10 to 200 nm although the preferablerange may be different depending on the used material.

(4) Light Emitting Layer

The light emitting layer in the organic EL device has a combination ofthe following functions (1) to (3).

(1) The injecting function: the function of injecting holes from theanode or the hole injecting layer and injecting electrons from thecathode or the electron injecting layer when an electric field isapplied.

(2) The transporting function: the function of transporting injectedcharges (i.e., electrons and holes) by the force of the electric field.

(3) The light emitting function: the function of providing the field forrecombination of electrons and holes and leading to the emission oflight.

However, the easiness of injection may be different between holes andelectrons and the ability of transportation expressed by the mobilitymay be different between holes and electrons. It is preferable thateither one of the charges be transferred.

For the process for forming the light emitting layer, a known processsuch as the vapor deposition process, the spin coating process, and theLB process can be used. It is particularly preferable that the lightemitting layer be a molecular deposit film. The molecular deposit filmis a thin film formed by deposition of a material compound in the gasphase or a film formed by solidification of a material compound in asolution or in the liquid phase. In general, the molecular deposit filmcan be distinguished from the thin film formed in accordance with the LBprocess (i.e., molecular accumulation film) based on the differences inaggregation structure and higher order structure and functionaldifferences caused by those structural differences.

Further, as disclosed in JP-A-57-51781, the light emitting layer canalso be formed by dissolving a binder such as a resin and the materialcompounds into a solvent to prepare a solution, followed by forming athin film from the prepared solution by the spin coating process or thelike.

In the present invention, where desired, the light emitting layer mayinclude other known light emitting materials other than the lightemitting material composed of the aromatic amine derivative of thepresent invention, or a light emitting layer including other known lightemitting material may be laminated to the light emitting layer includingthe light emitting material composed of the aromatic amine derivative ofthe present invention as long as the object of the present invention isnot adversely affected.

Examples of a light emitting material or a doping material which can beused in the light emitting layer together with the aromatic aminederivative of the present invention include, but not limited to,anthracene, naphthalene, phenanthrene, pyrene, tetracene, coronene,chrysene, fluoresceine, perylene, phthaloperylene, naphthaloperylene,perynone, phthaloperynone, naphthaloperynone, diphenylbutadiene,tetraphenylbutadiene, coumarin, oxadiazole, aldazine, bisbenzoxazoline,bisstyryl, pyrazine, cyclopentadiene, quinoline metal complexes,aminoquinoline metal complexes, benzoquinoline metal complexes, imine,diphenylethylene, vinylanthracene, diaminocarbazole, pyrane, thiopyrane,polymethine, merocyanine, imidazole-chelated oxynoid compounds,quinacridone, rubrene, and fluorescent dyes.

A host material that can be used in a light emitting layer together withthe aromatic amine derivative of the present invention is preferably acompound represented by any one of the following formulae (i) to (ix).

An asymmetric anthracene represented by the following general formula(i):

where:

Ar represents a substituted or unsubstituted fused aromatic group having10 to 50 ring carbon atoms;

Ar′ represents a substituted or unsubstituted aromatic group having 6 to50 ring carbon atoms;

X represents a substituted or unsubstituted aromatic group having 6 to50 ring carbon atoms, a substituted or unsubstituted aromaticheterocyclic group having 5 to 50 ring atoms, a substituted orunsubstituted alkyl group having 1 to 50 carbon atoms, a substituted orunsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted orunsubstituted aralkyl group having 6 to 50 carbon atoms, a substitutedor unsubstituted aryloxy group having 5 to 50 ring atoms, a substitutedor unsubstituted arylthio group having 5 to 50 ring atoms, a substitutedor unsubstituted alkoxycarbonyl group having 1 to 50 carbon atoms, acarboxyl group, a halogen atom, a cyano group, a nitro group, or ahydroxyl group.

a, b, and c each represent an integer of 0 to 4; and

n represents an integer of 1 to 3. In addition, when n represents 2 ormore, anthracene nuclei in H may be identical to or different from eachother.

An asymmetric monoanthracene derivative represented by the followinggeneral formula (ii):

where:

Ar¹ and Ar² each independently represent a substituted or unsubstitutedaromatic ring group having 6 to 50 ring carbon atoms. m and n eachrepresent an integer of 1 to 4; provided that Ar¹ and Ar² are notidentical to each other when m=n=1 and positions at which Ar¹ and Ar²are bound to a benzene ring are bilaterally symmetric, and m and nrepresent different integers when m or n represents an integer of 2 to4; and

R¹ to R¹⁰ each independently represent a hydrogen atom, a substituted orunsubstituted aromatic ring group having 6 to 50 ring carbon atoms, asubstituted or unsubstituted aromatic heterocyclic group having 5 to 50ring atoms, a substituted or unsubstituted alkyl group having 1 to 50carbon atoms, a substituted or unsubstituted cycloalkyl group, asubstituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, asubstituted or unsubstituted aralkyl group having 6 to 50 carbon atoms,a substituted or unsubstituted aryloxy group having 5 to 50 ring atoms,a substituted or unsubstituted arylthio group having 5 to 50 ring atoms,a substituted or unsubstituted alkoxycarbonyl group having 1 to 50carbon atoms, a substituted or unsubstituted silyl group, a carboxylgroup, a halogen atom, a cyano group, a nitro group, or a hydroxylgroup.

An asymmetric pyrene derivative represented by the following generalformula (iii):

where:

Ar and Ar′ each represent a substituted or unsubstituted aromatic grouphaving 6 to 50 ring carbon atoms;

L and L′ each represent a substituted or unsubstituted phenylene group,a substituted or unsubstituted naphthalenylene group, a substituted orunsubstituted fluorenylene group, or a substituted or unsubstituteddibenzosilolylene group;

m represents an integer of 0 to 2. n represents an integer of 1 to 4. srepresents an integer of 0 to 2. t represents an integer of 0 to 4; andin addition, L or Ar binds to any one of 1- to 5-positions of pyrene,and L′ or Ar′ binds to any one of 6- to 10-positions of pyrene;

provided that Ar, Ar′, L, and L′ satisfy the following item (1) or (2)when n+t represents an even number,

(1) Ar≠Ar′ and/or L≠L′ (where the symbol “≠” means that groups connectedwith the symbol have different structures)

(2) When Ar=Ar′ and L=L′,

(2-1) m 0 s and/or n 0 t, or

(2-2) when m=s and n=t,

-   -   (2-2-1) L and L′ or pyrene bind or binds to different binding        positions on Ar and Ar′, or    -   (2-2-2) in the case where L and L′ or pyrene bind or binds to        the same binding positions on Ar and Ar′, the case where the        substitution positions of L and L′, or of Ar and Ar′ in pyrene        are 1- and 6-positions, or 2- and 7-positions does not occur.

An asymmetric anthracene derivative represented by the following generalformula (iv):

where:

A¹ and A² each independently represent a substituted or unsubstitutedfused aromatic ring group having 10 to 20 ring carbon atoms;

Ar¹ and Ar² each independently represent a hydrogen atom, or

a substituted or unsubstituted aromatic ring group having 6 to 50 ringcarbon atoms;

R¹ to R¹⁰ each independently represent a hydrogen atom, a substituted orunsubstituted aromatic ring group having 6 to 50 ring carbon atoms, asubstituted or unsubstituted aromatic heterocyclic group having 5 to 50ring atoms, a substituted or unsubstituted alkyl group having 1 to 50carbon atoms, a substituted or unsubstituted cycloalkyl group, asubstituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, asubstituted or unsubstituted aralkyl group having 6 to 50 carbon atoms,a substituted or unsubstituted aryloxy group having 5 to 50 ring atoms,a substituted or unsubstituted arylthio group having 5 to 50 ring atoms,a substituted or unsubstituted alkoxycarbonyl group having 1 to 50carbon atoms, a substituted or unsubstituted silyl group, a carboxylgroup, a halogen atom, a cyano group, a nitro group, or a hydroxylgroup; and

the number of each of Ar¹, Ar², R⁹, and R¹⁰ may be two or more, andadjacent groups may form a saturated or unsaturated cyclic structure;

provided that the case where groups symmetric with respect to the X-Yaxis shown on central anthracene in the general formula (1) bind to 9-and 10-positions of the anthracene does not occur.

An anthracene derivative represented by the following general formula(v):

where: R¹ to R¹⁰ each independently represent a hydrogen atom, an alkylgroup, a cycloalkyl group, an aryl group which may be substituted, analkoxyl group, an aryloxy group, an alkylamino group, an alkenyl group,an arylamino group, or a heterocyclic group which may be substituted; aand b each represent an integer of 1 to 5, and, when a or b represents 2or more, R¹'s or R²'s may be identical to or different from each other,or R¹'s or R²'s may be bonded to each other to form a ring; R³ and R⁴,R⁵ and R⁶, R⁷ and R⁸, or R⁹ and R¹⁰ may be bonded to each other to forma ring; and L¹ represents a single bond, —O—, —S—, —N(R)— where Rrepresents an alkyl group or an aryl group which may be substituted, analkylene group, or an arylene group.

An anthracene derivative represented by the following general formula(vi):

where: R¹¹ to R²⁰ each independently represent a hydrogen atom, an alkylgroup, a cycloalkyl group, an aryl group, an alkoxyl group, an aryloxygroup, an alkylamino group, an arylamino group, or a heterocyclic groupwhich may be substituted; c, d, e, and f each represent an integer of 1to 5, and, when any one of c, d, e, and f represents 2 or more, R¹¹'s,R¹²'s, R¹⁶'s, or R¹⁷'s may be identical to or different from each other,or R¹¹'s, R¹²'s, R¹⁶'s, or R¹⁷'s may be bonded to each other to form aring; R¹³ and R¹⁴, or R¹⁸ and R¹⁹ may be bonded to each other to form aring; and L² represents a single bond, —O—, —S—, —N(R)— where Rrepresents an alkyl group or an aryl group which may be substituted, analkylene group, or an arylene group.

A spirofluorene derivative represented by the following general formula(vii):

where A⁵ to A⁸ each independently represent a substituted orunsubstituted biphenyl group, or a substituted or unsubstituted naphthylgroup.

A fused ring-containing compound represented by the following generalformula (viii):

where: A⁹ to A¹⁴ each have the same meaning as that described above; R²¹to R²³ each independently represent a hydrogen atom, an alkyl grouphaving 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbonatoms, an alkoxyl group having 1 to 6 carbon atoms, an aryloxy grouphaving 5 to 18 carbon atoms, an aralkyloxy group having 7 to 18 carbonatoms, an arylamino group having 5 to 16 carbon atoms, a nitro group, acyano group, an ester group having 1 to 6 carbon atoms, or a halogenatom; and at least one of A⁹ to A¹⁴ represents a group having three ormore fused aromatic rings.

A fluorene compound represented by the following general formula (ix):

where: R₁ and R₂ each represent a hydrogen atom, a substituted orunsubstituted alkyl group, a substituted or unsubstituted aralkyl group,a substituted or unsubstituted aryl group, a substituted orunsubstituted heterocyclic group, a substituted amino group, a cyanogroup, or a halogen atom; R₁'s or R₂'s bonded to different fluorenegroups may be identical to or different from each other, and R₁ and R₂bonded to the same fluorene group may be identical to or different fromeach other; R₃ and R₄ each represent a hydrogen atom, a substituted orunsubstituted alkyl group, a substituted or unsubstituted aralkyl group,a substituted or unsubstituted aryl group, or a substituted orunsubstituted heterocyclic group; R₃'s or R₄'s bonded to differentfluorene groups may be identical to or different from each other, and R₃and R₄ bonded to the same fluorene group may be identical to ordifferent from each other; Ar₁ and Ar₂ each represent a substituted orunsubstituted fused polycyclic aromatic group having three or morebenzene rings in total, or a substituted or unsubstituted fusedpolycyclic heterocyclic group that has three or more rings each of whichis a benzene ring or a heterocyclic ring in total and that is bonded toa fluorene group by carbon, and Ar₁ and Ar₂ may be identical to ordifferent from each other; and n represents an integer of 1 to 10.

Of the above-mentioned host materials, an anthracene derivative ispreferable, a monoanthracene derivative is more preferable, and anasymmetric anthracene is particularly preferable.

In addition, a phosphorescent compound can also be used as a lightemitting material for a dopant. A compound containing a carbazole ringas a host material is preferable as the phosphorescent compound. Thedopant is a compound capable of emitting light from a triplet exciton,and is not particularly limited as long as light is emitted from atriplet exciton, a metal complex containing at least one metal selectedfrom the group consisting of Ir, Ru, Pd, Pt, Os, and Re is preferable,and a porphyrin metal complex or an orthometalated metal complex ispreferable.

A host composed of a compound containing a carbazole ring and suitablefor phosphorescence is a compound having a function of causing aphosphorescent compound to emit light as a result of the occurrence ofenergy transfer from the excited state of the host to the phosphorescentcompound. A host compound is not particularly limited as long as it is acompound capable of transferring exciton energy to a phosphorescentcompound, and can be appropriately selected in accordance with apurpose. The host compound may have, for example, an arbitraryheterocyclic ring in addition to a carbazole ring.

Specific examples of such a host compound include a carbazolederivative, a triazole derivative, an oxazole derivative, an oxadiazolederivative, an imidazole derivative, a polyarylalkane derivative, apyrazoline derivative, a pyrazolone derivative, a phenylene diaminederivative, an aryl amine derivative, an amino substituted chalconederivative, a styrylanthracene derivative, a fluorenone derivative, ahydrazone derivative, a stilbene derivative, a silazane derivative, anaromatic tertiary amine compound, a styryl amine compound, an aromaticdimethylidene-based compound, a porphyrin-based compound, ananthraquinodimethane derivative, an anthrone derivative, adiphenylquinone derivative, a thiopyranedioxide derivative, acarbodiimide derivative, a fluorenilidene methane derivative, a distyrylpyrazine derivative, a heterocyclic tetracarboxylic anhydride such asnaphthaleneperylene, a phthalocyanine derivative, various metal complexpolysilane-based compounds typified by a metal complex of an8-quinolinol derivative or a metal complex having metal phthalocyanine,benzooxazole, or benzothiazole as a ligand, and polymer compounds suchas a poly(N-vinylcarbazole) derivative, an aniline-based copolymer, aconductive high molecular weight oligomer such as a thiophene oligomeror polythiophene, a polythiophene derivative, a polyphenylenederivative, a polyphenylene vinylene derivative, and a polyfluorenederivative. One of the host materials may be used alone, or two or moreof them may be used in combination.

Specific examples thereof include the compounds as described below.

A phosphorescent dopant is a compound capable of emitting light from atriplet exciton. The dopant, which is not particularly limited as longas light is emitted from a triplet exciton, is preferably a metalcomplex containing at least one metal selected from the group consistingof Ir, Ru, Pd, Pt, Os, and Re, and is preferably a porphyrin metalcomplex or an orthometalated metal complex. A porphyrin platinum complexis preferable as the porphyrin metal complex. One kind of aphosphorescent compound may be used alone, or two or more kinds ofphosphorescent compounds may be used in combination.

Any one of various ligands can be used for forming an orthometalatedmetal complex. Examples of a preferable ligand include a2-phenylpyridine derivative, a 7,8-benzoquinoline derivative, a2-(2-thienyl)pyridine derivative, a 2-(1-naphthyl)pyridine derivative,and a 2-phenylquinoline derivative. Each of those derivatives may have asubstituent as required. A fluoride of any one of those derivatives, orone obtained by introducing a trifluoromethyl group into any one ofthose derivatives is a particularly preferable blue-based dopant. Themetal complex may further include a ligand other than theabove-mentioned ligands such as acetylacetonate or picric acid as anauxiliary ligand.

The content of the phosphorescent dopant in the light emitting layer isnot particularly limited, and can be appropriately selected inaccordance with a purpose. The content is, for example, 0.1 to 70 mass%, and is preferably 1 to 30 mass %. When the content of thephosphorescent compound is less than 0.1 mass %, the intensity ofemitted light is weak, and an effect of the incorporation of thecompound is not sufficiently exerted. When the content exceeds 70 mass%, a phenomenon referred to as concentration quenching becomesremarkable, and device performance reduces.

In addition, the light emitting layer may contain a hole transportingmaterial, an electron transporting material, or a polymer binder asrequired.

Further, the thickness of the light emitting layer is preferably 5 to 50nm, more preferably 7 to 50 nm, or most preferably 10 to 50 nm. When thethickness is less than 5 nm, it becomes difficult to form the lightemitting layer, so the adjustment of chromaticity may be difficult. Whenthe thickness exceeds 50 nm, the voltage at which the device is drivenmay increase.

(5) Hole Injecting and Transporting Layer (Hole Transporting Zone)

The hole injecting and transporting layer is a layer which helpsinjection of holes into the light emitting layer and transports theholes to the light emitting region. The layer exhibits a great mobilityof holes and, in general, has an ionization energy as small as 5.5 eV orsmaller. For such the hole injecting and transporting layer, a materialwhich transports holes to the light emitting layer under an electricfield of a smaller strength is preferable. A material which exhibits,for example, a mobility of holes of at least 10⁻⁴ m²/V·sec underapplication of an electric field of 10⁴ to 10⁶ V/cm is preferable.

When the aromatic amine derivative of the present invention is used inthe hole transporting zone, the aromatic amine derivative of the presentinvention may be used alone or as a mixture with other materials forforming the hole injecting and transporting layer.

The material which can be used for forming the hole injecting andtransporting layer as a mixture with the aromatic amine derivative ofthe present invention is not particularly limited as long as thematerial has a preferable property described above. The material can bearbitrarily selected from materials which are conventionally used as thecharge transporting material of holes in photoconductive materials andknown materials which are used for the hole injecting and transportinglayer in organic EL devices.

Specific examples include: a triazole derivative (see, for example, U.S.Pat. No. 3,112,197); an oxadiazole derivative (see, for example, U.S.Pat. No. 3,189,447); an imidazole derivative (see, for example,JP-B-37-16096); a polyarylalkane derivative (see, for example, U.S. Pat.No. 3,615,402, U.S. Pat. No. 3,820,989, U.S. Pat. No. 3,542,544,JP-B-45-555, JP-B-51-10983, JP-A-51-93224, JP-A-55-17105, JP-A-56-4148,JP-A-55-108667, JP-A-55-156953, and JP-A-56-36656); a pyrazolinederivative and a pyrazolone derivative (see, for example, U.S. Pat. No.3,180,729, U.S. Pat. No. 4,278,746, JP-A-55-88064, JP-A-55-88065,JP-A-49-105537, JP-A-55-51086, JP-A-56-80051, JP-A-56-88141,JP-A-57-45545, JP-A-54-112637, and JP-A-55-74546); a phenylenediaminederivative (see, for example, U.S. Pat. No. 3,615,404, JP-B-51-10105,JP-B-46-3712, JP-B-47-25336, JP-A-54-53435, JP-A-54-110536, andJP-A-54-119925); an arylamine derivative (see, for example, U.S. Pat.No. 3,567,450, U.S. Pat. No. 3,180,703, U.S. Pat. No. 3,240,597, U.S.Pat. No. 3,658,520, U.S. Pat. No. 4,232,103, U.S. Pat. No. 4,175,961,U.S. Pat. No. 4,012,376, JP-B-49-35702, JP-B-39-27577, JP-A-55-144250,JP-A-56-119132, JP-A-56-22437, and DE 1,110,518); an amino-substitutedchalcone derivative (see, for example, U.S. Pat. No. 3,526,501); anoxazole derivative (those disclosed in U.S. Pat. No. 3,257,203); astyrylanthracene derivative (see, for example, JP-A-56-46234); afluorenone derivative (see, for example, JP-A-54-110837); a hydrazonederivative (see, for example, U.S. Pat. No. 3,717,462, JP-A-54-59143,JP-A-55-52063, JP-A-55-52064, JP-A-55-46760, JP-A-55-85495,JP-A-57-11350, JP-A-57-148749, and JP-A-2-311591); a stilbene derivative(see, for example, JP-A-61-210363, JP-A-61-228451, JP-A-61-14642,JP-A-61-72255, JP-A-62-47646, JP-A-62-36674, JP-A-62-10652,JP-A-62-30255, JP-A-60-93445, JP-A-60-94462, JP-A-60-174749, andJP-A-60-175052); a silazane derivative (U.S. Pat. No. 4,950,950); apolysilane-based copolymer (JP-A-2-204996); an aniline-based copolymer(JP-A-2-282263); and a conductive high molecular weight oligomer(particularly a thiophene oligomer) disclosed in JP-A-1-211399.

In addition to the above-mentioned materials which can be used as thematerial for the hole injecting and transporting layer, a porphyrincompound (those disclosed in, for example, JP-A-63-2956965); an aromatictertiary amine compound and a styrylamine compound (see, for example,U.S. Pat. No. 4,127,412, JP-A-53-27033, JP-A-54-58445, JP-A-54-149634,JP-A-54-64299, JP-A-55-79450, JP-A-55-144250, JP-A-56-119132,JP-A-61-295558, JP-A-61-98353, and JP-A-63-295695) are preferable, andaromatic tertiary amines are particularly preferable.

Further examples of aromatic tertiary amine compounds include compoundshaving two fused aromatic rings in the molecule such as4,4′-bis(N-(1-naphthyl)-N-phenylamino)-biphenyl (hereinafter referred toas NPD) as disclosed in U.S. Pat. No. 5,061,569, and a compound in whichthree triphenylamine units are bonded together in a star-burst shape,such as 4,4′,4″-tris(N-(3-methylphenyl)-N-phenylamino)-triphenylamine(hereinafter referred to as MTDATA) as disclosed in JP-A-4-308688.

Further, in addition to the aromatic dimethylidene-based compoundsdescribed above as the material for the light emitting layer, inorganiccompounds such as Si of the p-type and SiC of the p-type can also beused as the material for the hole injecting and transporting layer.

The hole injecting and transporting layer can be formed by forming athin layer from the aromatic amine derivative of the present inventionin accordance with a known process such as the vacuum vapor depositionprocess, the spin coating process, the casting process, and the LBprocess. The thickness of the hole injecting and transporting layer isnot particularly limited. In general, the thickness is 5 nm to 5 μm. Thehole injecting and transporting layer may be constituted of a singlelayer containing one or more materials described above or may be alaminate constituted of hole injecting and transporting layerscontaining materials different from the materials of the hole injectingand transporting layer described above as long as the aromatic aminederivative of the present invention is incorporated in the holeinjecting and transporting zone.

Further, an organic semiconductor layer may be disposed as a layer forhelping the injection of holes or electrons into the light emittinglayer. As the organic semiconductor layer, a layer having a conductivityof 10¹⁰ S/cm or greater is preferable. As the material for the organicsemiconductor layer, oligomers containing thiophene, and conductiveoligomers such as oligomers containing arylamine and conductivedendrimers such as dendrimers containing arylamine which are disclosedin JP-A-08-193191, can be used.

(6) Electron Injecting and Transporting Layer

Next, the electron injecting and transporting layer is a layer whichhelps injection of electrons into the light emitting layer, transportsthe electrons to the light emitting region, and exhibits a greatmobility of electrons. The adhesion improving layer is an electroninjecting layer including a material exhibiting particularly improvedadhesion with the cathode.

In addition, it is known that, in an organic EL device, emitted light isreflected by an electrode (cathode in this case), so emitted lightdirectly extracted from an anode and emitted light extracted via thereflection by the electrode interfere with each other. The thickness ofan electron transporting layer is appropriately selected from the rangeof several nanometers to several micrometers in order that theinterference effect may be effectively utilized. When the thickness isparticularly large, an electron mobility is preferably at least 10⁻⁵m²/Vs or more upon application of an electric field of 10⁴ to 10⁶ V/cmin order to avoid an increase in voltage.

A metal complex of 8-hydroxyquinoline or of a derivative of8-hydroxyquinoline, or an oxadiazole derivative is suitable as amaterial to be used in an electron injecting layer. Specific examples ofthe metal complex of 8-hydroxyquinoline or of a derivative of8-hydroxyquinoline that can be used as an electron injecting materialinclude metal chelate oxynoid compounds each containing a chelate ofoxine (generally 8-quinolinol or 8-hydroxyquinoline) such astris(8-quinolinolato) aluminum.

On the other hand, examples of the oxadiazole derivative includeelectron transfer compounds represented by the following generalformulae:

where: Ar¹, Ar², Ar³, Ar⁵, Ar⁶ and Ar⁹ each represent a substituted orunsubstituted aryl group and may represent the same group or differentgroups. Ar⁴, Ar⁷ and Ar⁸ each represent a substituted or unsubstitutedarylene group and may represent the same group or different groups.

Examples of the aryl group include a phenyl group, a biphenyl group, ananthranyl group, a perylenyl group, and a pyrenyl group. Examples of thearylene group include a phenylene group, a naphthylene group, abiphenylene group, an anthranylene group, a perylenylene group, and apyrenylene group. Examples of the substituent include alkyl groups eachhaving 1 to 10 carbon atoms, alkoxyl groups each having 1 to 10 carbonatoms, and a cyano group. As the electron transfer compound, compoundswhich can form thin films are preferable.

Examples of the electron transfer compounds described above include thefollowing.

Further, materials represented by the following general formulae (A) to(E) can be used in an electron injecting layer and an electrontransporting layer.

Nitrogen-containing heterocyclic derivatives represented by the generalformulae (A) and (B)

In the general formulae (A) and (B), A¹ to A³ each independentlyrepresent a nitrogen atom or a carbon atom, Ar¹ represents a substitutedor unsubstituted aryl group having 6 to 60 ring carbon atoms, or asubstituted or unsubstituted heteroaryl group having 3 to 60 ring carbonatoms, Ar² represents a hydrogen atom, a substituted or unsubstitutedaryl group having 6 to 60 ring carbon atoms, a substituted orunsubstituted heteroaryl group having 3 to 60 ring carbon atoms, asubstituted or unsubstituted alkyl group having 1 to 20 carbon atoms, ora substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms,or a divalent group of any one of them provided that one of Ar¹ and Ar²represents a substituted or unsubstituted fused ring group having 10 to60 ring carbon atoms or a substituted or unsubstituted monohetero fusedring group having 3 to 60 ring carbon atoms, L¹, L², and L eachindependently represent a single bond, a substituted or unsubstitutedarylene group having to 60 ring carbon atoms, a substituted orunsubstituted heteroarylene group having 3 to 60 ring carbon atoms, or asubstituted or unsubstituted fluorenylene group, R represents a hydrogenatom, a substituted or unsubstituted aryl group having 6 to 60 ringcarbon atoms, a substituted or unsubstituted heteroaryl group having 3to 60 ring carbon atoms, a substituted or unsubstituted alkyl grouphaving 1 to 20 carbon atoms, or a substituted or unsubstituted alkoxygroup having 1 to 20 carbon atoms. n represents an integer of 0 to 5,and, when n represents 2 or more, multiple R's may be identical to ordifferent from each other, and multiple R groups adjacent to each othermay be bonded to each other to form a carbocyclic aliphatic ring or acarbocyclic aromatic ring.)

A nitrogen-containing heterocyclic ring derivative represented by thegeneral formula (C):

HAr-L-Ar¹—Ar²  (C)

In the formula, HAr represents a nitrogen-containing heterocyclic ringwhich has 3 to 40 carbon atoms and may have a substituent, L representsa single bond, an arylene group which has 6 to 60 carbon atoms and mayhave a substituent, a heteroarylene group which has 3 to 60 carbon atomsand may have a substituent, or a fluorenylene group which may have asubstituent, Ar¹ represents a divalent aromatic hydrocarbon group whichhas 6 to 60 carbon atoms and may have a substituent, and Ar² representsan aryl group which has 6 to 60 carbon atoms and may have a substituent,or a heteroaryl group which has 3 to 60 carbon atoms and may have asubstituent.

A silacyclopentadiene derivative represented by the general formula (D):

where; X and Y each independently represent a saturated or unsaturatedhydrocarbon group having 1 to 6 carbon atoms, an alkoxy group, analkenyloxy group, an alkynyloxy group, a hydroxy group, a substituted orunsubstituted aryl group, or a substituted or unsubstituted heterocycle,or X and Y are bonded to each other to form a structure as a saturatedor unsaturated ring; and R₁ to R₄ each independently represent hydrogen,a halogen atom, a substituted or unsubstituted alkyl group having 1 to 6carbon atoms, an alkoxy group, an aryloxy group, a perfluoroalkyl group,a perfluoroalkoxy group, an amino group, an alkylcarbonyl group, anarylcarbonyl group, an alkoxycarbonyl group, an aryloxycarbonyl group,an azo group, an alkylcarbonyloxy group, an arylcarbonyloxy group, analkoxycarbonyloxy group, an aryloxycarbonyloxy group, a sulfinyl group,a sulfonyl group, a sulfanyl group, a silyl group, carbamoyl group, anaryl group, a heterocyclic group, an alkenyl group, an alkynyl group, anitro group, a formyl group, a nitroso group, a formyloxy group, anisocyano group, a cyanate group, an isocyanate group, a thiocyanategroup, an isothiocyanate group, or a cyano group, or, when two or moreof R₁ to R₄ are adjacent to each other, they form a structure in which asubstituted or unsubstituted ring is condensed.

A borane derivative represented by the general formula (E):

where; R₁ to R₈ and Z₂ each independently represent a hydrogen atom, asaturated or unsaturated hydrocarbon group, an aromatic group, aheterocyclic group, a substituted amino group, a substituted borylgroup, an alkoxy group, or an aryloxy group; X, Y, and Z₁ eachindependently represent a saturated or unsaturated hydrocarbon group, anaromatic group, a heterocyclic group, a substituted amino group, analkoxy group, or an aryloxy group; substituents of Z₁ and Z₂ may bebonded to each other to form a fused ring; and n represents an integerof 1 to 3, and, when n represents 2 or more, Z₁'s may be different fromeach other provided that the case where n represents 1, X, Y, and R₂each represent a methyl group, R₈ represents a hydrogen atom or asubstituted boryl group and the case where n represents 3 and Z₁'s eachrepresent a methyl group are excluded.

In the equation (F): Q¹ and Q² each independently represent a ligandrepresented by the following general formula (G); and L represents ahalogen atom, a substituted or unsubstituted alkyl group, a substitutedor unsubstituted cycloalkyl group, a substituted or unsubstituted arylgroup, a substituted or unsubstituted heterocyclic group, —OR¹ where R¹represents a hydrogen atom, a substituted or unsubstituted alkyl group,a substituted or unsubstituted cycloalkyl group, a substituted orunsubstituted aryl group, or a substituted or unsubstituted heterocyclicgroup, or a ligand represented by —O—Ga-Q³ (Q⁴) where Q³ and Q⁴ areidentical to Q¹ and Q², respectively.)

In the equation (G): the rings A¹ and A² are six-membered aryl ringstructures which are condensed with each other and each of which mayhave a substituent.

The metal complex behaves strongly as an n-type semiconductor, and has alarge electron injecting ability. Further, generation energy uponformation of the complex is low. As a result, the metal and the ligandof the formed metal complex are bonded to each other so strongly thatthe fluorescent quantum efficiency of the complex as a light emittingmaterial improves.

Specific examples of a substituent in the rings A¹ and A² which eachform a ligand in the general formula (G) include: a halogen atom such aschlorine, bromine, iodine, or fluorine; a substituted or unsubstitutedalkyl group such as a methyl group, an ethyl group, a propyl group, abutyl group, an s-butyl group, a t-butyl group, a pentyl group, a hexylgroup, a heptyl group, an octyl group, a stearyl group, ortrichloromethyl group; a substituted or unsubstituted aryl group such asa phenyl group, a naphthyl group, a 3-methylphenyl group, a3-methoxyphenyl group, a 3-fluorophenyl group, a 3-trichloromethylphenylgroup, a 3-trifluoromethylphenyl group, or a 3-nitrophenyl group; asubstituted or unsubstituted alkoxy group such as a methoxy group, ann-butoxy group, a t-butoxy group, a trichloromethoxy group, atrifluoroethoxy group, a pentafluoropropoxy group, a2,2,3,3-tetrafluoropropoxy group, an 1,1,1,3,3,3-hexafluoro-2-propoxygroup, or a 6-(perfluoroethyl)hexyloxy group; a substituted orunsubstituted aryloxy group such as a phenoxy group, a p-nitrophenoxygroup, p-t-butylphenoxy group, a 3-fluorophenoxy group, apentafluorophenyl group, or a 3-trifluoromethylphenoxy group; asubstituted or unsubstituted alkylthio group such as a methylthio group,an ethylthio group, a t-butylthio group, a hexylthio group, an octylthiogroup, or a trifluoromethylthio group; a substituted or unsubstitutedarylthio group such as a phenylthio group, a p-nitrophenylthio group, ap-t-butylphenylthio group, a 3-fluorophenylthio group, apentafluorophenylthio group, or a 3-trifluoromethylphenylthio group; amono-substituted or di-substituted amino group such as a cyano group, anitro group, an amino group, a methylamino group, a dimethylamino group,an ethylamino group, a diethylamino group, a dipropylamino group, adibutylamino group, or a diphenylamino group; an acylamino group such asa bis(acetoxymethyl)amino group, a bis(acetoxyethyl)amino group, abis(acetoxypropyl)amino group, or a bis(acetoxybutyl)amino group; ahydroxyl group; a siloxy group; an acyl group; a carbamoyl group such asa methylcarbamoyl group, a dimethylcarbamoyl group, an ethylcarbamoylgroup, a diethylcarbamoyl group, a propylcarbamoyl group, abutylcarbamoyl group, or a phenylcarbamoyl group; a cycloalkyl groupsuch as a carboxylic acid group, a sulfonic acid group, an imide group,a cyclopentane group, or a cyclohexyl group; an aryl group such as aphenyl group, a naphthyl group, a biphenyl group, an anthranyl group, aphenanthryl group, a fluorenyl group, or a pyrenyl group; and aheterocyclic group such as a pyridinyl group, a pyrazinyl group, apyrimidinyl group, a pyridazinyl group, a triazinyl group, an indolinylgroup, a quinolinyl group, an acridinyl group, a pyrrolidinyl group, adioxanyl group, a piperidinyl group, a morpholidinyl group, apiperazinyl group, a triathinyl group, a carbazolyl group, a furanylgroup, a thiophenyl group, an oxazolyl group, an oxadiazolyl group, abenzoxazolyl group, a thiazolyl group, a thiadiazolyl group, abenzothiazolyl group, a triazolyl group, an imidazolyl group, abenzoimidazolyl group, or a puranyl group. In addition, theabove-mentioned substituents may be bound to each other to further forma six-membered aryl ring or a heterocycle.

A preferable embodiment of the organic EL device of the presentinvention includes an element including a reducing dopant in the regionof electron transport or in the interfacial region of the cathode andthe organic thin film layer. The reducing dopant is defined as asubstance which can reduce a compound having the electron-transportingproperty. Various compounds can be used as the reducing dopant as longas the compounds have a uniform reductive property. For example, atleast one substance selected from the group consisting of alkali metals,alkaline earth metals, rare earth metals, alkali metal oxides, alkalimetal halides, alkaline earth metal oxides, alkaline earth metalhalides, rare earth metal oxides, rare earthmetal halides, organiccomplexes of alkali metals, organic complexes of alkaline earth metals,and organic complexes of rare earth metals can be preferably used.

More specifically, examples of the reducing dopant include substanceshaving a work function of 2.9 eV or smaller, specific examples of whichinclude at least one alkali metal selected from the group consisting ofNa (the work function: 2.36 eV), K (the work function: 2.28 eV), Rb (thework function: 2.16 eV), and Cs (the work function: 1.95 eV) and atleast one alkaline earth metal selected from the group consisting of Ca(the work function: 2.9 eV), Sr (the work function: 2.0 to 2.5 eV), andBa (the work function: 2.52 eV). Among the above-mentioned substances,at least one alkali metal selected from the group consisting of K, Rb,and Cs is more preferable, Rb and Cs are still more preferable, and Csis most preferable as the reducing dopant. Those alkali metals havegreat reducing ability, and the luminance of the emitted light and thelife time of the organic EL device can be increased by addition of arelatively small amount of the alkali metal into the electron injectingzone. As the reducing dopant having a work function of 2.9 eV orsmaller, combinations of two or more alkali metals thereof are alsopreferable. Combinations having Cs such as the combinations of Cs andNa, Cs and K, Cs and Rb, and Cs, Na, and K are more preferable. Thereducing ability can be efficiently exhibited by the combination havingCs. The luminance of emitted light and the life time of the organic ELdevice can be increased by adding the combination having Cs into theelectron injecting zone.

The present invention may further include an electron injecting layerwhich is composed of an insulating material or a semiconductor anddisposed between the cathode and the organic layer. At this time, leakof electric current can be effectively prevented by the electroninjecting layer and the electron injecting property can be improved. Asthe insulating material, at least one metal compound selected from thegroup consisting of alkali metal chalcogenides, alkaline earth metalchalcogenides, alkali metal halides, and alkaline earth metal halides ispreferable. It is preferable that the electron injecting layer becomposed of the above-mentioned substance such as the alkali metalchalcogenide since the electron injecting property can be furtherimproved. Preferable examples of the alkali metal chalcogenide includeLi₂O, K₂O, Na₂S, Na₂Se, and Na₂O. To be specific, preferable examples ofthe alkaline earth metal chalcogenide include CaO, BaO, SrO, BeO, BaS,and CaSe. Preferable examples of the alkali metal halide include LiF,NaF, KF, LiCl, KCl, and NaCl. Preferable examples of the alkaline earthmetal halide include fluorides such as CaF₂, BaF₂, SrF₂, MgF₂, and BeF₂and halides other than the fluorides.

Examples of the semiconductor composing the electron-transporting layerinclude oxides, nitrides, and oxide nitrides of at least one elementselected from Ba, Ca, Sr, Yb, Al, Ga, In, Li, Na, Cd, Mg, Si, Ta, Sb,and Zn used alone or in combination of two or more. It is preferablethat the inorganic compound composing the electron-transporting layerforms a crystallite or amorphous insulating thin film. When the electroninjecting layer is composed of the insulating thin film described above,a more uniform thin film can be formed, and defects of pixels such asdark spots can be decreased. Examples of the inorganic compound includealkali metal chalcogenides, alkaline earth metal chalcogenides, alkalimetal halides, and alkaline earth metal halides which are describedabove.

(7) Cathode

As the cathode, a material such as a metal, an alloy, a conductivecompound, or a mixture of those materials which has a small workfunction (4 eV or smaller) is used because the cathode is used forinjecting electrons to the electron injecting and transporting layer orthe light emitting layer. Specific examples of the electrode materialinclude sodium, sodium-potassium alloys, magnesium, lithium,magnesium-silver alloys, aluminum/aluminum oxide, aluminum-lithiumalloys, indium, and rare earth metals.

The cathode can be prepared by forming a thin film of the electrodematerial described above in accordance with a process such as the vapordeposition process and the sputtering process.

When the light emitted from the light emitting layer is obtained throughthe cathode, it is preferable that the cathode have a transmittance ofthe emitted light greater than 10%.

It is also preferable that the sheet resistivity of the cathode beseveral hundred Ω/□ or smaller. The thickness of the cathode is, ingeneral, selected in the range of 10 nm to 1 μm and preferably in therange of 50 to 200 nm.

(8) Insulating Layer

Defects in pixels tend to be formed in organic EL device due to leak andshort circuit since an electric field is applied to ultra-thin films. Toprevent the formation of the defects, a layer of a thin film having aninsulating property is preferably inserted between the pair ofelectrodes.

Examples of the material used for the insulating layer include aluminumoxide, lithium fluoride, lithium oxide, cesium fluoride, cesium oxide,magnesium oxide, magnesium fluoride, calcium oxide, calcium fluoride,aluminum nitride, titanium oxide, silicon oxide, germanium oxide,silicon nitride, boron nitride, molybdenum oxide, ruthenium oxide, andvanadium oxide. Mixtures and laminates of the above-mentioned compoundsmay also be used.

(9) Method of Producing the Organic EL Device

To prepare the organic EL device of the present invention, the anode andthe light emitting layer, and, where necessary, the hole injecting andthe transporting layer and the electron injecting and transporting layerare formed in accordance with the illustrated process using theillustrated materials, and the cathode is formed in the last step. Theorganic EL device may also be prepared by forming the above-mentionedlayers in the order reverse to that described above, i.e., the cathodebeing formed in the first step and the anode in the last step.

Hereinafter, an embodiment of the process for preparing an organic ELdevice having a construction in which an anode, a hole injecting layer,a light emitting layer, an electron injecting layer, and a cathode aredisposed successively on a substrate transmitting light will bedescribed.

On a suitable transparent substrate, a thin film made of a material forthe anode is formed in accordance with the vapor deposition process orthe sputtering process so that the thickness of the formed thin film is1 μm or smaller and preferably in the range of 10 to 200 nm. The formedthin film is used as the anode. Then, a hole injecting layer is formedon the anode. The hole injecting layer can be formed in accordance withthe vacuum vapor deposition process, the spin coating process, thecasting process, or the LB process, as described above. The vacuum vapordeposition process is preferable since a uniform film can be easilyobtained and the possibility of formation of pin holes is small. Whenthe hole injecting layer is formed in accordance with the vacuum vapordeposition process, in general, it is preferable that the conditions besuitably selected in the following ranges: the temperature of the sourceof the deposition: 50 to 450° C.; the vacuum: 10⁻⁷ to 10⁻³ Torr; therate of deposition: 0.01 to 50 nm/second; the temperature of thesubstrate: −50 to 300° C. and the thickness of the film: 5 nm to 5 μm;although the conditions of the vacuum, vapor deposition are differentdepending on the compound to be used (i.e., the material for the holeinjecting layer) and the crystal structure and the recombinationstructure of the target hole injecting layer.

Then, the light emitting layer is formed on the hole injecting layerformed above. A thin film of the organic light emitting material can beformed by using a desired organic light emitting material in accordancewith a process such as the vacuum vapor deposition process, thesputtering process, the spin coating process, or the casting process,and the formed thin film is used as the light emitting layer. The vacuumvapor deposition process is preferable since a uniform film can beeasily obtained and the possibility of formation of pin holes is small.When the light emitting layer is formed in accordance with the vacuumvapor deposition process, in general, the conditions of the vacuum vapordeposition process can be selected in the same ranges as those describedfor the vacuum vapor deposition of the hole injecting layer, althoughthe conditions are different depending on the used compound.

Next, an electron injecting layer is formed on the light emitting layerformed above. Similarly to the hole injecting layer and the lightemitting layer, it is preferable that the electron injecting layer beformed in accordance with the vacuum vapor deposition process since auniform film must be obtained. The conditions of the vacuum vapordeposition can be selected in the same ranges as those described for thevacuum vapor deposition of the hole injecting layer and the lightemitting layer.

When the vapor deposition process is used, the aromatic amine derivativeof the present invention can be deposited by vapor in combination withother materials, although the situation may be different depending onwhich layer in the light emitting zone or in the hole transporting zoneincludes the compound. When the spin coating process is used, thecompound can be incorporated into the formed layer by using a mixture ofthe compound with other materials.

A cathode is formed on the electron injecting layer formed above in thelast step, and an organic EL device can be obtained.

The cathode is made of a metal and can be formed in accordance with thevacuum vapor deposition process or the sputtering process. It ispreferable that the vacuum vapor deposition process be used in order toprevent formation of damages on the lower organic layers during theformation of the film.

In the above-mentioned preparation of the organic EL device, it ispreferable that the above-mentioned layers from the anode to the cathodebe formed successively while the preparation system is kept in a vacuumafter being evacuated once.

The method of forming the layers in the organic EL device of the presentinvention is not particularly limited. A conventionally known processsuch as the vacuum vapor deposition process or the spin coating processcan be used. The organic thin film layer which is used in the organic ELdevice of the present invention and includes the compound represented bygeneral formula (1) described above can be formed in accordance with aknown process such as the vacuum vapor deposition process or themolecular beam epitaxy process (the MBE process) or, using a solutionprepared by dissolving the compounds into a solvent, in accordance witha coating process such as the dipping process, the spin coating process,the casting process, the bar coating process, or the roll coatingprocess.

The thickness of each layer in the organic thin film layer in theorganic EL device of the present invention is not particularly limited.In general, an excessively thin layer tends to have defects such as pinholes, and an excessively thick layer requires a high applied voltage todecrease the efficiency. Therefore, a thickness in the range of severalnanometers to 1 μm is preferable.

The organic EL device which can be prepared as described above emitslight when a direct voltage of 5 to 40 V is applied in the conditionthat the polarity of the anode is positive (+) and the polarity of thecathode is negative (−). When the polarity is reversed, no electriccurrent is observed and no light is emitted at all. When an alternatingvoltage is applied to the organic EL device, the uniform light emissionis observed only in the condition that the polarity of the anode ispositive and the polarity of the cathode is negative. When analternating voltage is applied to the organic EL device, any type ofwave shape can be used.

EXAMPLES

Hereinafter, the present invention will be described in more detail onthe basis of synthesis examples and examples.

Synthesis Example 1 Synthesis of Intermediate 1

20.0 g of 4-bromobiphenyl (manufactured by TOKYO CHEMICAL INDUSTRY CO.,LTD.), 8.64 g of sodium t-butoxide (manufactured by Wako Pure ChemicalIndustries, Ltd.), and 84 mg of palladium acetate (manufactured by WakoPure Chemical Industries, Ltd.) were loaded into a 200-mL three-neckedflask. Further, a stirring rod was placed in the flask, and rubber capswere set on both side ports of the flask. A reflux condenser wasinserted into the central port of the flask, and a three-way cock and aballoon in which an argon gas was sealed were set above the condenser.The inside of the system was replaced with the argon gas in the balloonthree times by using a vacuum pump.

Next, 120 mL of dehydrated toluene (manufactured by HIROSHIMA WAKO CO.,LTD.), 4.08 mL of benzylamine (manufactured by TOKYO CHEMICAL INDUSTRYCO., LTD.), and 338 μL of tri-t-butylphosphine (manufactured bySIGMA-ALDRICH, 2.22-mol/L toluene solution) were added to the flask byusing a syringe through a rubber septum, and the whole was stirred for 5minutes at room temperature.

Next, the flask was set in an oil bath, and was gradually heated to 120°C. while the solution was stirred. At 7 hours after that, the flask waslifted off the oil bath so that the reaction would be completed. Theflask was left under an argon atmosphere for 12 hours.

The reaction solution was transferred to a separating funnel, and 600 mLof dichloromethane were added to dissolve the precipitate. After theresultant had been washed with 120 mL of a saturated salt solution, anorganic layer was dried with anhydrous potassium carbonate. The solventof the organic layer obtained by separating potassium carbonate byfiltration was removed by distillation. 400 mL of toluene and 80 mL ofethanol were added to the resultant residue. A drying pipe was attachedto heat the resultant to 80° C. so that the residue would be completelydissolved. After that, the resultant was left for 12 hours, and wasslowly cooled to room temperature for recrystallization.

The precipitated crystal was separated by filtration, and was dried in avacuum at 60° C., whereby 13.5 g of N, N-di-(4-biphenylyl)benzylaminewere obtained.

1.35 g of N,N-di-(4-biphenylyl)benzylamine and 135 mg ofpalladium-activated carbon (manufactured by HIROSHIMA WAKO CO., LTD.,palladium content 10 wt %) were loaded into a 300-mL one-necked flask,and 100 mL of chloroform and 20 mL of ethanol were added to dissolve themixture.

Next, a stirring rod was placed in the flask. After that, a three-waycock mounted with a balloon filled with 2 L of a hydrogen gas wasattached to the flask, and the inside of the flask system was replacedwith the hydrogen gas ten times by using a vacuum pump. The balloon wasnewly filled with a hydrogen gas in an amount corresponding to thereduced amount so that the volume of the hydrogen gas would be 2 Lagain. After that, the solution was vigorously stirred at roomtemperature for 30 hours. After that, 100 mL of dichloromethane wereadded to the resultant, and the catalyst was separated by filtration.

Next, the resultant solution was transferred to a separating funnel, andwas washed with 50 mL of a saturated aqueous solution of sodiumhydrogencarbonate. After that, an organic layer was fractionated anddried with anhydrous potassium carbonate. After the resultant had beenfiltrated, the solvent was removed by distillation, and 50 mL of toluenewere added to the resultant residue for recrystallization. Theprecipitated crystal was separated by filtration, and was dried in avacuum at 50° C., whereby 0.99 g of di-4-biphenylylamine(Intermediate 1) shown below was obtained.

Synthesis Example 2 Synthesis of Intermediate 2

In a stream of argon, 10 g of di-4-biphenylylamine, 9.7 g of4,4′-dibromobiphenyl (manufactured by TOKYO CHEMICAL INDUSTRY CO.,LTD.), 3 g of sodium t-butoxide (manufactured by HIROSHIMA WAKO CO.,LTD.), 0.5 g of bis(triphenylphosphine) palladium (II) chloride(manufactured by TOKYO CHEMICAL INDUSTRY CO., LTD.), and 500 mL ofxylene were loaded, and the whole was subjected to a reaction at 130° C.for 24 hours.

After the resultant had been cooled, 1,000 mL of water were added to theresultant, and the mixture was subjected to Celite filtration. Thefiltrate was extracted with toluene and dried with anhydrous magnesiumsulfate. The dried product was condensed under reduced pressure, and theresultant crude product was subjected to column purification. Thepurified product was recrystallized with toluene. The crystal was takenby filtration, and was then dried, whereby 4.6 g of4′-bromo-N,N-dibiphenylyl-4-amino-1,1′-biphenyl (Intermediate 2) shownbelow were obtained.

Synthesis Example 3 Synthesis of Intermediate 3

In a stream of argon, 6.8 g of N-phenyl-1-naphthylamine (manufactured byTOKYO CHEMICAL INDUSTRY CO., LTD.), 9.7 g of 4,4′-dibromobiphenyl(manufactured by TOKYO CHEMICAL INDUSTRY CO., LTD.), 3 g of t-butoxysodium (manufactured by HIROSHIMA WAKO CO., LTD.), 0.5 g ofbis(triphenylphosphine)palladium(II) chloride (manufactured by TOKYOCHEMICAL INDUSTRY CO., LTD.), and 500 mL of xylene were loaded, and thewhole was subjected to a reaction at 130° C. for 24 hours.

After the resultant had been cooled, 1,000 mL of water were added to theresultant, and the mixture was subjected to Celite filtration. Thefiltrate was extracted with toluene and dried with anhydrous magnesiumsulfate. The dried product was condensed under reduced pressure, and theresultant crude product was subjected to column purification. Thepurified product was recrystallized with toluene. The crystal was takenby filtration, and was then dried, whereby 4.1 g of4′-bromo-N-phenyl-N-1-naphthyl-amino-1,1′-biphenyl (Intermediate 3)shown below were obtained.

Synthesis Example 4 Synthesis of Intermediate 4 and Intermediate 5

250 g of m-terphenyl (manufactured by SIGMA-ALDRICH), 50 g of hydroiodicacid dihydrate, 75 g of iodine, 750 mL of acetic acid, and 25 mL ofconcentrated sulfuric acid were loaded into a three-necked flask, andthe whole was subjected to a reaction at 70° C. for 3 hours. After thereaction, the resultant was injected into 5 L of methanol, and then thewhole was stirred for 1 hour. The resultant crystal taken by thefiltration of the mixture was purified by means of column chromatographyand recrystallized with acetonitrile, whereby 64 g of5-phenyl-3-iodobiphenyl (Intermediate 4) shown below and 17 g of3′-phenyl-4-iodobiphenyl (Intermediate 5) shown below were obtained.

Synthesis Example 5 Synthesis of Intermediate 6

Under an argon atmosphere, 50 g of 2-bromofluorene (manufactured byTOKYO CHEMICAL INDUSTRY CO., LTD.), 100 mL of dimethylsulfoxide (DMSO),0.95 g of benzyltriethylammonium chloride (manufactured by HIROSHIMAWAKO CO., LTD.), and 65 g of a 50-wt % aqueous solution of sodiumhydroxide were loaded into a 1,000-mL three-necked flask.

The reaction vessel was placed in a water bath, and 44 g of1,5-dibromopentane (manufactured by HIROSHIMA WAKO CO., LTD.) were addedto the mixture while the mixture was stirred.

After a reaction for 5 hours, 1,000 mL of water were added to theresultant, and the whole was extracted with 500 mL of toluene. Anorganic layer was dried with magnesium sulfate, and the solvent wasremoved by distillation with a rotary evaporator, whereby 56 g ofIntermediate 6 shown below as oil were obtained.

Synthesis Example 6 Synthesis of Intermediate 7

A reaction was performed in the same manner as in Synthesis Example 5except that 47 g of 1,6-dibromohexane (manufactured by HIROSHIMA WAKOCO., LTD.) were used instead of 1,5-dibromopentane. As a result, 49 g ofIntermediate 7 shown below as oil were obtained.

Synthesis Example 7 Synthesis of Intermediate 8

In a stream of argon, 5.7 g of benzamide (manufactured by TOKYO CHEMICALINDUSTRY CO., LTD.), 10 g of 4-bromobiphenyl (manufactured by TOKYOCHEMICAL INDUSTRY CO., LTD.), 0.82 g of copper (I) iodide (manufacturedby HIROSHIMA WAKO CO., LTD.), 0.76 g of N,N′-dimethylethylenediamine(manufactured by SIGMA-ALDRICH), 11.8 g of potassium carbonate(manufactured by HIROSHIMA WAKO Co., LTD.), and 60 mL of xylene wereloaded into a 200-mL three-necked flask, and the whole was subjected toa reaction at 130° C. for 36 hours.

After having been cooled, the resultant was filtrated and washed withtoluene. Further, the resultant was washed with water and methanol.After that, the resultant was dried, whereby 10.5 g of Intermediate 8shown below as a pale yellow powder were obtained.

Synthesis Example 8 Synthesis of Intermediate 9

In a stream of argon, 11.1 g of 1-acetamidenaphthalene (manufactured byTOKYO CHEMICAL INDUSTRY CO., LTD.), 15.4 g of 4-bromobiphenyl(manufactured by TOKYOCHEMICAL INDUSTRY CO., LTD.), 1.14 g of copper(I)iodide (manufactured by HIROSHIMA WAKO CO., LTD.), 1.06 g ofN,N′-dimethylethylenediamine (manufactured by SIGMA-ALDRICH), 20.0 g ofpotassium carbonate (manufactured by HIROSHIMA WAKO CO., LTD.), and 100mL of xylene were loaded into a 300-mL three-necked flask, and the wholewas subjected to a reaction at 130° C. for 36 hours.

After having been cooled, the resultant was filtrated and washed withtoluene. Further, the resultant was washed with water and methanol.After that, the resultant was dried, whereby 15.0 g of a pale yellowpowder were obtained.

15.0 g of the above-mentioned powder, 17.6 g of potassium hydroxide(manufactured by HIROSHIMA WAKO CO., LTD.), 15 mL of ion-exchangedwater, 20 mL of xylene (manufactured by HIROSHIMA WAKO CO., LTD.), and10 mL of ethanol (manufactured by HIROSHIMA WAKO CO., LTD.) were loadedinto a 300-mL three-necked flask, and the whole was refluxed for 36hours. After the completion of the reaction, the resultant was extractedwith toluene and dried with magnesium sulfate. The dried product wascondensed under reduced pressure, and the resultant crude product wassubjected to column purification. The purified product wasrecrystallized with toluene. The crystal was taken by filtration, andwas then dried, whereby 11.2 g of Intermediate 9 shown below as a whitepowder were obtained.

Synthesis Example 9 Synthesis of Intermediate 10

A reaction was performed in the same manner as in Synthesis Example 8except that 25.6 g of Intermediate 4 were used instead of 15.4 g of4-bromobiphenyl (manufactured by TOKYO CHEMICAL INDUSTRY CO., LTD.). Asa result, 11.3 g of Intermediate 10 shown below as a white powder wereobtained.

Synthesis Example 10 Synthesis of Intermediate 11

A reaction was performed in the same manner as in Synthesis Example 8except that 25.6 g of Intermediate 5 were used instead of 15.4 g of4-bromobiphenyl (manufactured by TOKYO CHEMICAL INDUSTRY CO., LTD.). Asa result, 10.6 g of Intermediate 11 shown below as a white powder wereobtained.

Synthesis Example 11 Synthesis of Intermediate 12

A reaction was performed in the same manner as in Synthesis Example 8except that 20.6 g of Intermediate 7 were used instead of 15.4 g of4-bromobiphenyl (manufactured by TOKYO CHEMICAL INDUSTRY CO., LTD.). Asa result, 11.9 g of Intermediate 12 shown below as a white powder wereobtained.

Synthesis Example 12 Synthesis of Intermediate 13

In a stream of argon, 16.4 g of Intermediate 8, 17.0 g of9-bromophenanthrene (manufactured by TOKYO CHEMICAL INDUSTRY CO., LTD.),1.14 g of copper(I) iodide (manufactured by HIROSHIMA WAKO CO., LTD.),1.06 g of N,N′-dimethylethylenediamine (manufactured by SIGMA-ALDRICH),20.0 g of potassium carbonate (manufactured by HIROSHIMA WAKO CO.,LTD.), and 100 mL of xylene were loaded into a 300-mL three-neckedflask, and the whole was subjected to a reaction at 130° C. for 36hours.

After having been cooled, the resultant was filtrated and washed withtoluene. Further, the resultant was washed with water and methanol.After that, the resultant was dried, whereby 14.0 g of a pale yellowpowder were obtained.

14.0 g of the above-mentioned powder, 15.1 g of potassium hydroxide(manufactured by HIROSHIMA WAKO CO., LTD.), 13 mL of ion-exchangedwater, 17 mL of xylene (manufactured by HIROSHIMA WAKO CO., LTD.), and 9mL of ethanol (manufactured by HIROSHIMA WAKO CO., LTD.) were loadedinto a 300-mL three-necked flask, and the whole was refluxed for 36hours. After the completion of the reaction, the resultant was extractedwith toluene and dried with magnesium sulfate. The dried product wascondensed under reduced pressure, and the resultant crude product wassubjected to column purification. The purified product wasrecrystallized with toluene. The crystal was taken by filtration, andwas then dried, whereby 9.3 g of Intermediate 13 shown below as a whitepowder were obtained.

Synthesis Example 13 Synthesis of Intermediate 14)

A reaction was performed in the same manner as in Synthesis Example 12except that 20.7 g of Intermediate 4 were used instead of 17.0 g of9-bromophenanthrene (manufactured by TOKYO CHEMICAL INDUSTRY CO., LTD.).As a result, 15.1 g of Intermediate 14 shown below as a white powderwere obtained.

Synthesis Example 14 Synthesis of Intermediate 15

A reaction was performed in the same manner as in Synthesis Example 12except that 20.7 g of Intermediate 5 were used instead of 17.0 g of9-bromophenanthrene (manufactured by TOKYO CHEMICAL INDUSTRY CO., LTD.).As a result, 14.3 g of Intermediate 15 shown below as a white powderwere obtained.

Synthesis Example 15 Synthesis of Intermediate 16

A reaction was performed in the same manner as in Synthesis Example 12except that 20.6 g of Intermediate 7 were used instead of 17.0 g of9-bromophenanthrene (manufactured by TOKYO CHEMICAL INDUSTRY CO., LTD.).As a result, 11.5 g of Intermediate 16 shown below as a white powderwere obtained.

Synthesis Example 16 Synthesis of Intermediate 17

A reaction was performed in the same manner as in Synthesis Example 12except that 19.7 g of Intermediate 6 were used instead of 17.0 g of9-bromophenanthrene (manufactured by TOKYO CHEMICAL INDUSTRY CO., LTD.).As a result, 10.5 g of Intermediate 17 shown below as a white powderwere obtained.

Synthesis Example 17 Synthesis of Intermediate 18

A reaction was performed in the same manner as in Synthesis Example 12except that 18.0 g of 2-bromo-9,9-dimethylflorene were used instead of17.0 g of 9-bromophenanthrene (manufactured by TOKYO CHEMICAL INDUSTRYCO., LTD.). As a result, 10.6 g of Intermediate 18 shown below as awhite powder were obtained.

Synthesis Example 18 Synthesis of Intermediate 19

In a stream of argon, 7.2 g of benzamide (manufactured by TOKYO CHEMICALINDUSTRY CO., LTD.), 40.8 g of Intermediate 5, 2.3 g of copper(I) iodide(manufactured by HIROSHIMA WAKO CO., LTD.), 2.1 g ofN,N′-dimethylethylenediamine (manufactured by SIGMA-ALDRICH), 33.1 g ofpotassium carbonate (manufactured by HIROSHIMA WAKO CO., LTD.), and 100mL of xylene were loaded into a 200-mL three-necked flask, and the wholewas subjected to a reaction at 130° C. for 36 hours.

After having been cooled, the resultant was filtrated and washed withtoluene. Further, the resultant was washed with water and methanol.After that, the resultant was dried, whereby 27.0 g of a pale yellowpowder were obtained.

27.0 g of the above-mentioned powder, 19.0 g of potassium hydroxide(manufactured by HIROSHIMA WAKO CO., LTD.), 17 mL of ion-exchangedwater, 25 mL of xylene (manufactured by HIROSHIMA WAKO CO., LTD.), and12 mL of ethanol (manufactured by HIROSHIMA WAKO CO., LTD.) were loadedinto a 300-mL three-necked flask, and the whole was refluxed for 36hours. After the completion of the reaction, the resultant was extractedwith toluene and dried with magnesium sulfate. The dried product wascondensed under reduced pressure, and the resultant crude product wassubjected to column purification. The purified product wasrecrystallized with toluene. The crystal was taken by filtration, andwas then dried, whereby 18.1 g of Intermediate 19 shown below as a whitepowder were obtained.

Synthesis Example 19 Synthesis of Intermediate 20

A reaction was performed in the same manner as in Synthesis Example 18except that 41.3 g of 2-bromo-9,9-dimethylfluorene were used instead of40.8 g of Intermediate 5. As a result, 15.3 g of Intermediate 20 shownbelow as a white powder were obtained.

Synthesis Example 20 Synthesis of Intermediate 21

In a stream of argon, 28.6 g of 1-bromonaphthalene, 80 mL of dehydratedether, and 80 mL of dehydrated toluene were loaded into a 500-mLthree-necked flask. 110 mmol of a solution of n-butyllithium in hexanewere charged into the mixture at −30° C., and the whole was subjected toa reaction at 0° C. for 1 hour. The resultant was cooled to −70° C., and70 mL of triisopropyl borate were loaded into the resultant. Theresultant was slowly heated to room temperature and stirred for 1 hour.80 mL of 10% hydrochloric acid were added to the resultant, and thewhole was extracted with ethyl acetate/water. After that, the extractwas dried with anhydrous sodium sulfate. The solution was condensed andwashed with hexane, whereby 17.5 g of a boric acid compound wereobtained.

In a stream of argon, 17.5 g of the boric acid compound obtained in theforegoing, 11.0 g of bromobenzene, 3.8 g oftetrakis(triphenylphosphine)palladium(0), 100 mL of a 2-M Na₂CO₃solution, and 160 mL of dimethoxyethane were loaded into a 500-mLthree-necked flask, and then the whole was refluxed for 8 hours. Thereaction liquid was extracted with toluene/water and dried withanhydrous sodium sulfate. The dried product was condensed under reducedpressure, and the resultant crude product was subjected to columnpurification, whereby 17.6 g of Intermediate 21 shown below as a whitepowder were obtained. FD-MS analysis resulted in 1:1 peaks at m/z=282and 284 for C₁₆H₁₁Br=283, so the resultant powder was identified asIntermediate 21 shown below.

Synthesis Example 21 Synthesis of Intermediate 22

A reaction was performed in the same manner as in Synthesis Example 20except that 20.7 g of 4-bromobiphenyl were used instead of 20.7 g ofbromobenzene. As a result, 7.4 g of Intermediate 22 shown below as awhite powder were obtained. FD-MS analysis resulted in 1:1 peaks atm/z=358 and 360 for C₂₂H₁₅Br=359, so the resultant powder was identifiedas Intermediate 22 shown below.

Synthesis Example 22 Synthesis of Intermediate 23

In a stream of argon, 20.7 g of 1-bromonaphthalene, 80 mL of dehydratedether, and 80 mL of dehydrated toluene were loaded into a 500-mLthree-necked flask. 120 mmol of a solution of n-butyllithium in hexanewere charged into the mixture at −30° C., and the whole was subjected toa reaction at 0° C. for 1 hour. The resultant was cooled to −70° C., and70 mL of triisopropyl borate were loaded into the resultant. Theresultant was slowly heated to room temperature and stirred for 1 hour.80 mL of 10% hydrochloric acid were added to the resultant, and thewhole was extracted with ethyl acetate and water. After that, theextract was dried with anhydrous sodium sulfate. The solution wascondensed and washed with hexane, whereby 9.7 g of a boric acid compoundwere obtained.

In a stream of argon, 9.7 g of the boric acid compound obtained in theforegoing, 13.3 g of 4-iodobromobenzene, 1.9 g oftetrakis(triphenylphosphine)palladium(0), 50 mL of a 2-M sodiumcarbonate solution, and 80 mL of dimethoxyethane were loaded into a500-mL three-necked flask, and then the whole was refluxed for 8 hours.The reaction liquid was extracted with toluene/water and dried withanhydrous sodium sulfate. The dried product was condensed under reducedpressure, and the resultant crude product was subjected to columnpurification, whereby 8.8 g of Intermediate 23 shown below as a whitepowder were obtained. FD-MS analysis resulted in 1:1 peaks at m/z=282and 284 for C₁₆H₁₁Br=283, so the resultant powder was identified asIntermediate 23 shown below.

Synthesis Example 23 Synthesis of Intermediate 24

A reaction was performed in the same manner as in Synthesis Example 22except that 20.7 g of 2-bromonaphthalene were used instead of 20.7 g of1-bromonaphthalene. As a result, 7.6 g of Intermediate 24 shown below asa white powder were obtained. FD-MS analysis resulted in 1:1 peaks atm/z=282 and 284 for C₁₆H₁₁Br=283, so the resultant powder was identifiedas Intermediate 24 shown below.

Synthesis Example 24 Synthesis of Intermediate 25

A reaction was performed in the same manner as in Synthesis Example 22except that 34.0 g of 4′-iodobromobenzene were used instead of 26.5 g of4-iodobromobenzene. As a result, 10.1 g of Intermediate 25 shown belowas a white powder were obtained. FD-MS analysis resulted in 1:1 peaks atm/z=358 and 360 for C₂₂H₁₅Br=359, so the resultant powder was identifiedas Intermediate 25 shown below.

Synthesis Example 25 Synthesis of Intermediate 26

A reaction was performed in the same manner as in Synthesis Example 7except that 21.4 g of 2-bromonaphthalene were used instead of 10 g of4-bromobiphenyl, and then a hydrolysis was performed in the same manneras in Synthesis Example 8. As a result, 8.1 g of Intermediate 26 shownbelow as a white powder were obtained. FD-MS analysis resulted in a mainpeak at m/z=269 for C₂₀H₁₅Br=269, so the resultant powder was identifiedas Intermediate 26 shown below.

Synthesis Example 26 Synthesis of Intermediate 27

A reaction was performed in the same manner as in Synthesis Example 7except that 26.1 g of Intermediate 23 were used instead of 10 g of4-bromobiphenyl, and then a hydrolysis was performed in the same manneras in Synthesis Example 8. As a result, 8.1 g of Intermediate 27 shownbelow as a white powder were obtained. FD-MS analysis resulted in a mainpeak at m/z=421 for C₃₂H₃₂Br=421, so the resultant powder was identifiedas Intermediate 27 shown below.

Synthesis Example 27 Synthesis of Intermediate 28

A reaction was performed in the same manner as in Synthesis Example 2except that: 7.6 g of 4-amino-p-terphenyl were used instead of 10 g ofdi-4-biphenylylamine; and 9.6 g of 4-bromo-p-terphenyl were used insteadof 9.7 g of 4,4′-dibromobiphenyl. As a result, 6.2 g of Intermediate 28shown below as a white powder were obtained. FD-MS analysis resulted ina main peak at m/z=473 for C₃₆H₂₇N=473, so the resultant powder wasidentified as Intermediate 28 shown below.

Synthesis Example 28 Synthesis of Intermediate 29

A reaction was performed in the same manner as in Synthesis Example 2except that: 2.9 g of aniline were used instead of 10 g ofdi-4-biphenylylamine; and 8.8 g of Intermediate 21 were used instead of9.7 g of 4,4′-dibromobiphenyl. As a result, 4.2 g of Intermediate 29shown below as a white powder were obtained. FD-MS analysis resulted ina main peak at m/z=295 for C₂₂H₁₇N=295, so the resultant powder wasidentified as Intermediate 29 shown below.

Synthesis Example 29 Synthesis of Intermediate 30

A reaction was performed in the same manner as in Synthesis Example 28except that 11.1 g of Intermediate 22 were used instead of 8.8 g ofIntermediate 21. As a result, 5.7 g of Intermediate 30 shown below as awhite powder were obtained. FD-MS analysis resulted in a main peak atm/z=371 for C₂₈H₂₁N=371, so the resultant powder was identified asIntermediate 30 shown below.

Synthesis Example 30 Synthesis of Intermediate 31

A reaction was performed in the same manner as in Synthesis Example 28except that 8.8 g of Intermediate 23 were used instead of 8.8 g ofIntermediate 21. As a result, 4.0 g of Intermediate 31 shown below as awhite powder were obtained. FD-MS analysis resulted in a main peak atm/z=295 for C₂₂H₁₇N=295, so the resultant powder was identified asIntermediate 31 shown below.

Synthesis Example 31 Synthesis of Intermediate 32

A reaction was performed in the same manner as in Synthesis Example 28except that 8.8 g of Intermediate 24 were used instead of 8.8 g ofIntermediate 21. As a result, 3.6 g of Intermediate 32 shown below as awhite powder were obtained. FD-MS analysis resulted in a main peak atm/z=295 for C₂₂H₁₇N=295, so the resultant powder was identified asIntermediate 32 shown below.

Synthesis Example 32 Synthesis of Intermediate 33

A reaction was performed in the same manner as in Synthesis Example 28except that 11.1 g of Intermediate 22 were used instead of 8.8 g ofIntermediate 21. As a result, 6.2 g of Intermediate 33 shown below as awhite powder were obtained. FD-MS analysis resulted in a main peak atm/z=371 for C₂₈H₂₁N=371, so the resultant powder was identified asIntermediate 33 shown below.

Synthesis Example 33 Synthesis of Intermediate 34

A reaction was performed in the same manner as in Synthesis Example 27except that 4.9 g of bromobenzene were used instead of 9.6 g of4-bromo-p-terphenyl. As a result, 3.9 g of Intermediate 34 shown belowas a white powder were obtained. FD-MS analysis resulted in a main peakat m/z=321 for C₂₄H₁₉N=321, so the resultant powder was identified asIntermediate 34 shown below.

Synthesis Example 34 Synthesis of Intermediate 35

A reaction was performed in the same manner as in Synthesis Example 27except that 6.4 g of 1-bromonaphthalene were used instead of 9.6 g of4-bromo-p-terphenyl. As a result, 3.8 g of Intermediate 34 shown belowas a white powder were obtained. FD-MS analysis resulted in a main peakat m/z=371 for C₂₈H₂₁N=371, so the resultant powder was identified asIntermediate 35 shown below.

Synthesis Example 35 Synthesis of Intermediate 36

In a stream of argon, 11.1 g of N-phenyl-1-naphthylamine, 15.6 g of4-iodobromobiphenyl, 1.9 g of copper (I) iodide (manufactured by WakoPure Chemical Industries, Ltd.), 2.0 g of N,N′-dimethylethylenediamine(manufactured by SIGMA-ALDRICH), 8.6 g of t-butoxysodium (manufacturedby TOKYO CHEMICAL INDUSTRY CO., LTD.), and 100 mL of dehydrated toluenewere loaded into a 300-mL three-necked flask, and the whole wassubjected to a reaction at 110° C. for 8 hours. After the completion ofthe reaction, the resultant was extracted with toluene and dried withmagnesium sulfate. The dried product was condensed under reducedpressure, and the resultant crude product was subjected to columnpurification. The purified product was recrystallized with toluene. Thecrystal was taken by filtration, and was then dried, whereby 16.8 g of awhite powder were obtained.

In a stream of argon, 16.8 g of the above-mentioned white powder and 100mL of dehydrated xylene were added to a 300-mL three-necked flask, andthe whole was cooled to −30° C. 30 mL of n-butyllithium (1.6-M hexanesolution) were charged into the mixture, and the whole was subjected toa reaction for 1 hour. After the resultant had been cooled to −70° C.,28 mL of triisopropyl borate (manufactured by TOKYO CHEMICAL INDUSTRYCO., LTD.) were loaded into the resultant. The resultant was slowlyheated, and was stirred at room temperature for 1 hour. 32 mL of a 10%hydrochloric acid solution were added to the resultant, and the wholewas stirred. The resultant was extracted with ethyl acetate and water,and an organic layer was washed with water. The resultant was dried withanhydrous sodium sulfate, and the solvent was removed by distillation.The resultant was washed with hexane, whereby 7.5 g of a white powderwere obtained.

Example of Synthesis 1 Synthesis of Compound H1

In a stream of argon, 3.1 g of Intermediate 1, 3.6 g of Intermediate 3,2.0 g of t-butoxysodium (manufactured by HIROSHIMA WAKO CO., LTD.), 0.33g of bis(triphenylphosphine) palladium (II) chloride (manufactured byTOKYO CHEMICAL INDUSTRY CO., LTD.), and 300 mL of xylene were loaded,and the whole was subjected to a reaction at 130° C. for 24 hours.

After having been cooled, the resultant was added with 500 ml of water,and the mixture was subjected to Celite filtration. The filtrate wasextracted with toluene and dried with anhydrous magnesium sulfate. Theresultant was concentrated under reduced pressure, and the resultantcrude product was subjected to column purification. Then, the resultantwas recrystallized with toluene, and the recrystallized product wasseparated by filtration and dried, thereby yielding 4.1 g of pale yellowpowder. The powder was identified as Compound H1 to be described belowbecause a main peak of m/z=690 was obtained for C₅₂H₃₈N₂=690 as a resultof FD-MS (field desorption mass spectrometry) analysis.

Example of Synthesis 2 Synthesis of Compound H2

A reaction was performed in the same manner as in Example of Synthesis 1except that 3.7 g of Intermediate 9 were used instead of Intermediate 1,thereby yielding 3.1 g of pale yellow powder. The powder was identifiedas Compound H2 to be described below because a main peak of m/z=664 wasobtained for C₅₀H₃₆N₂=664 as a result of FD-MS analysis.

Example of Synthesis 3 Synthesis of Compound H3

A reaction was performed in the same manner as in Example of Synthesis 1except that 4.3 g of Intermediate 13 were used instead of Intermediate1, thereby yielding 4.1 g of pale yellow powder. The powder wasidentified as Compound H3 to be described below because a main peak ofm/z=714 was obtained for C₅₄H₃₈N₂=714 as a result of FD-MS analysis.

Example of Synthesis 4 Synthesis of Compound H4

A reaction was performed in the same manner as in Example of Synthesis 1except that 3.6 g of Intermediate 10 were used instead of Intermediate1, thereby yielding 3.9 g of pale yellow powder. The powder wasidentified as Compound H4 to be described below because a main peak ofm/z=740 was obtained for C₅₆H₄₀N₂=740 as a result of FD-MS analysis.

Example of Synthesis 5 Synthesis of Compound H5

A reaction was performed in the same manner as in Example of Synthesis 1except that 3.6 g of Intermediate 10 were used instead of Intermediate 1and 4.4 g of Intermediate 2 were used instead of Intermediate 3, therebyyielding 4.1 g of pale yellow powder. The powder was identified asCompound H5 to be described below because a main peak of m/z=842 wasobtained for C₆₄H₄₆N₂=842 as a result of FD-MS analysis.

Example of Synthesis 6 Synthesis of Compound H6

A reaction was performed in the same manner as in Example of Synthesis 1except that 3.8 g of Intermediate 14 were used instead of Intermediate1, thereby yielding 3.7 g of pale yellow powder. The powder wasidentified as Compound H6 to be described below because a main peak ofm/z=766 was obtained for C₅₈H₄₂N₂=766 as a result of FD-MS analysis.

Example of Synthesis 7 Synthesis of Compound H7

A reaction was performed in the same manner as in Example of Synthesis 1except that 3.6 g of Intermediate 11 were used instead of Intermediate 1and 4.4 g of Intermediate 2 were used instead of Intermediate 3, therebyyielding 4.8 g of pale yellow powder. The powder was identified asCompound H7 to be described below because a main peak of m/z=842 wasobtained for C₆₄H₄₆N₂=842 as a result of FD-MS analysis.

Example of Synthesis 8 Synthesis of Compound H8

A reaction was performed in the same manner as in Example of Synthesis 1except that 3.8 g of Intermediate 15 were used instead of Intermediate1, thereby yielding 4.8 g of pale yellow powder. The powder wasidentified as Compound H8 to be described below because a main peak ofm/z=766 was obtained for C₅₈H₄₂N₂=766 as a result of FD-MS analysis.

Example of Synthesis 9 Synthesis of Compound H9

A reaction was performed in the same manner as in Example of Synthesis 1except that 4.5 g of Intermediate 19 were used instead of Intermediate1, thereby yielding 4.2 g of pale yellow powder. The powder wasidentified as Compound H9 to be described below because a main peak ofm/z=842 was obtained for C₆₄H₄₆N₂=842 as a result of FD-MS analysis.

Example of Synthesis 10 Synthesis of Compound H10

A reaction was performed in the same manner as in Example of Synthesis 1except that 3.6 g of Intermediate 12 were used instead of Intermediate1, thereby yielding 4.2 g of pale yellow powder. The powder wasidentified as Compound H10 to be described below because a main peak ofm/z=744 was obtained for C₅₆H₄₄N₂=744 as a result of FD-MS analysis.

Example of Synthesis 11 Synthesis of Compound H11

A reaction was performed in the same manner as in Example of Synthesis 1except that 3.6 g of Intermediate 12 were used instead of Intermediate 1and 4.4 g of Intermediate 2 were used instead of Intermediate 3, therebyyielding 4.1 g of pale yellow powder. The powder was identified asCompound H11 to be described below because a main peak of m/z=846 wasobtained for C₆₄H₅₀N₂=846 as a result of FD-MS analysis.

Example of Synthesis 12 Synthesis of Compound H12

A reaction was performed in the same manner as in Example of Synthesis 1except that 3.8 g of Intermediate 16 were used instead of Intermediate1, thereby yielding 4.5 g of pale yellow powder. The powder wasidentified as Compound H12 to be described below because a main peak ofm/z=770 was obtained for C₅₈H₄₆N₂=770 as a result of FD-MS analysis.

Example of Synthesis 13 Synthesis of Compound H13)

A reaction was performed in the same manner as in Example of Synthesis 1except that 4.6 g of Intermediate 20 were used instead of Intermediate1, thereby yielding 4.2 g of pale yellow powder. The powder wasidentified as Compound H13 to be described below because a main peak ofm/z=850 was obtained for C₆₄H₅₄N₂=850 as a result of FD-MS analysis.

Example of Synthesis 14 Synthesis of Compound H14

A reaction was performed in the same manner as in Example of Synthesis 1except that 3.7 g of Intermediate 17 were used instead of Intermediate1, thereby yielding 4.2 g of pale yellow powder. The powder wasidentified as Compound H14 to be described below because a main peak ofm/z=756 was obtained for C₅₇H₄₄N₂=756 as a result of FD-MS analysis.

Example of Synthesis 15 Synthesis of Compound H15

A reaction was performed in the same manner as in Example of Synthesis 1except that 3.5 g of Intermediate 18 were used instead of Intermediate1, thereby yielding 3.9 g of pale yellow powder. The powder wasidentified as Compound H15 to be described below because a main peak ofm/z=730 was obtained for C₅₅H₄₂N₂=730 as a result of FD-MS analysis.

Example of Synthesis 16 Synthesis of Compound H16

A reaction was performed in the same manner as in Example of Synthesis 1except that 2.7 g of Intermediate 26 were used instead of Intermediate1, thereby yielding 3.1 g of pale yellow powder. The powder wasidentified as Compound H16 to be described below because a main peak ofm/z=638 was obtained for C₄₈H₃₄N₂=638 as a result of FD-MS analysis.

Example of Synthesis 17 Synthesis of Compound H17

A reaction was performed in the same manner as in Example of Synthesis 1except that 4.2 g of Intermediate 27 were used instead of Intermediate1, thereby yielding 4.1 g of pale yellow powder. The powder wasidentified as Compound H17 to be described below because a main peak ofm/z=790 was obtained for C₆₀H₄₂N₂=790 as a result of FD-MS analysis.

Example of Synthesis 18 Synthesis of Compound H18

A reaction was performed in the same manner as in Example of Synthesis 1except that 4.7 g of Intermediate 28 were used instead of Intermediate1, thereby yielding 3.9 g of pale yellow powder. The powder wasidentified as Compound H18 to be described below because a main peak ofm/z=842 was obtained for C₆₄H₄₆N₂=842 as a result of FD-MS analysis.

Example of Synthesis 19 Synthesis of Compound H19

A reaction was performed in the same manner as in Example of Synthesis 5except that 3.0 g of Intermediate 29 were used instead of Intermediate10, thereby yielding 3.0 g of pale yellow powder. The powder wasidentified as Compound H19 to be described below because a main peak ofm/z=766 was obtained for C₅₈H₄₂N₂=766 as a result of FD-MS analysis.

Example of Synthesis 20 Synthesis of Compound H20

A reaction was performed in the same manner as in Example of Synthesis 5except that 3.7 g of Intermediate 30 were used instead of Intermediate10, thereby yielding 2.8 g of pale yellow powder. The powder wasidentified as Compound H20 to be described below because a main peak ofm/z=843 was obtained for C₆₄H₄₆N₂=843 as a result of FD-MS analysis.

Example of Synthesis 21 Synthesis of Compound H21

A reaction was performed in the same manner as in Example of Synthesis 5except that 3.0 g of Intermediate 31 were used instead of Intermediate10, thereby yielding 2.9 g of pale yellow powder. The powder wasidentified as Compound H21 to be described below because a main peak ofm/z=766 was obtained for C₅₈H₄₂N₂=766 as a result of FD-MS analysis.

Example of Synthesis 22 Synthesis of Compound H22

A reaction was performed in the same manner as in Example of Synthesis 5except that 3.0 g of Intermediate 32 were used instead of Intermediate10, thereby yielding 3.2 g of pale yellow powder. The powder wasidentified as Compound H22 to be described below because a main peak ofm/z=766 was obtained for C₅₈H₄₂N₂=766 as a result of FD-MS analysis.

Example of Synthesis 23 Synthesis of Compound H23

A reaction was performed in the same manner as in Example of Synthesis 5except that 3.7 g of Intermediate 33 were used instead of Intermediate10, thereby yielding 3.1 g of pale yellow powder. The powder wasidentified as Compound H23 to be described below because a main peak ofm/z=843 was obtained for C₆₄H₄₆N₂=843 as a result of FD-MS analysis.

Example of Synthesis 24 Synthesis of Compound H24

A reaction was performed in the same manner as in Example of Synthesis 5except that 3.2 g of Intermediate 34 were used instead of Intermediate10, thereby yielding 3.6 g of pale yellow powder. The powder wasidentified as Compound H24 to be described below because a main peak ofm/z=793 was obtained for C₆₀H₄₄N₂=793 as a result of FD-MS analysis.

Example of Synthesis 25 Synthesis of Compound H25

A reaction was performed in the same manner as in Example of Synthesis 5except that 3.7 g of Intermediate 35 were used instead of Intermediate10, thereby yielding 3.5 g of pale yellow powder. The powder wasidentified as Compound H25 to be described below because a main peak ofm/z=843 was obtained for C₆₄H₄₆N₂=843 as a result of FD-MS analysis.

Example of Synthesis 26 Synthesis of Compound H26

In a stream of argon, 3.4 g of Intermediate 36, 5.4 of Intermediate 2,0.26 g of tetrakis(triphenylphosphine)palladium(0), 3.18 g of sodiumcarbonate, 50 mL of 1,2-dimethoxyethane, and 30 mL of water were addedto a 300-mL three-necked flask, and the whole was refluxed for 8 hours.The resultant was extracted with toluene, and an organic layer waswashed with water. The resultant was dried with anhydrous sodiumsulfate, and the solvent was removed by distillation. The resultant wasrecrystallized with toluene/hexane, whereby 3.6 g of a pale yellowpowder were obtained. FD-MS analysis resulted in a main peak at m/z=766for C₅₈H₄₂N₂=766, so the resultant powder was identified as Compound H26described below.

Example 1 Production of Organic EL Device

A glass substrate with an ITO transparent electrode measuring 25 mm wideby 75 mm long by 1.1 mm thick (manufactured by GEOMATEC Co., Ltd.) wassubjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes.After that, the substrate was subjected to UV ozone cleaning for 30minutes.

The glass substrate with the transparent electrode line after thewashing was mounted on a substrate holder of a vacuum deposition device.First, Compound H232 to be described below was formed into a film havinga thickness of 60 nm on the surface on the side where the transparentelectrode line was formed to cover the transparent electrode. The H232film functions as a hole injecting layer. Compound H1 described above,as a hole transporting material, was formed into a film having athickness of 20 nm on the H232 film. The film functions as a holetransporting layer. Further, Compound EM1 to be described below wasdeposited from the vapor and formed into a film having a thickness of 40nm. Simultaneously with this formation, Amine Compound D1 having astyryl group to be described below, as a light emitting molecule, wasdeposited from the vapor in such a manner that a weight ratio betweenCompound EM1 and Amine Compound D1 would be 40:2. The film functions asa light emitting layer.

Alq to be described below was formed into a film having a thickness of10 nm on the resultant film. The film functions as an electron injectinglayer. After that, Li serving as a reducing dopant (Li source:manufactured by SAES Getters) and Alq were subjected to co-deposition.Thus, an Alq:Li film (having a thickness of 10 nm) was formed as anelectron injecting layer (cathode). Metal Al was deposited from thevapor onto the Alq:Li film to form a metal cathode. Thus, an organic ELdevice was formed.

In addition, the current efficiency of the resultant organic EL devicewas measured, and the luminescent color of the device was observed. Acurrent efficiency at 10 mA/cm² was calculated by measuring a luminanceby using a CS1000 manufactured by Minolta. Further, the half lifetime oflight emission in DC constant current driving at an initial luminance of5,000 cd/m² and room temperature was measured. Table 1 shows the resultsthereof.

Examples 2 to 26 Production of Organic EL Devices

Organic EL devices were each produced in the same manner as in Example 1except that any one of the compounds shown in Table 1 was used as a holetransporting material instead of Compound H1.

Comparative Example 1

An organic EL device was produced in the same manner as in Example 1except that Comparative Compound 1 was used as a hole transportingmaterial instead of Compound H1.

The current efficiency of the resultant organic EL device was measured,and the luminescent color of the device was observed. Further, the halflifetime of light emission in DC constant current driving at an initialluminance of 5,000 cd/m² and room temperature was measured. Table 1shows the results thereof.

TABLE 1 Hole Current transporting efficiency Luminescent Half lifetimeExample material (cd/A) color (hour)  1 H1 5 Blue 41  2 H2 4.8 Blue 390 3 H3 4.6 Blue 370  4 H4 5.5 Blue 350  5 H5 5.4 Blue 340  6 H6 5.5 Blue350  7 H7 5.2 Blue 370  8 H8 5.3 Blue 380  9 H9 5.1 Blue 390 10 H10 5.1Blue 340 11 H11 5.3 Blue 360 12 H12 5.2 Blue 340 13 H13 5 Blue 330 14H14 5.1 Blue 350 15 H15 5 Blue 330 16 H16 5.4 Blue 320 17 H17 5.2 Blue420 18 H18 5.1 Blue 410 19 H19 4.9 Blue 400 20 H20 4.9 Blue 410 21 H215.3 Blue 380 22 H22 5.2 Blue 390 23 H23 5.0 Blue 360 24 H24 5.1 Blue 38025 H25 4.9 Blue 410 26 H26 5.3 Blue 330 Comparative Comparative 4.8 Blue260 Example 1 Compound 1

Example 27 Production of Organic EL Device

An organic EL device was produced in the same manner as in Example 1except that Arylamine Compound D2 to be described below was used insteadof Amine Compound D1 having a styryl group. Me represents a methylgroup.

The measured current efficiency of the resultant organic EL device was5.2 cd/A, and the luminescent color of the device was blue. Further, thehalf lifetime of light emission in DC constant current driving at aninitial luminance of 5,000 cd/m² and room temperature was measured. Themeasured half lifetime was 400 hours.

Comparative Example 2

An organic EL device was produced in the same manner as in Example 27except that Comparative Compound 1 described above was used instead ofCompound H1 as a hole transporting material.

The measured current efficiency of the resultant organic EL device was4.9 cd/A, and the luminescent color of the device was blue. Further, thehalf lifetime of light emission in DC constant current driving at aninitial luminance of 5,000 cd/m² and room temperature was measured. Themeasured half lifetime was 230 hours.

As can be seen from the above-mentioned results, the use of the aromaticamine derivative of the present invention as a hole transportingmaterial for an organic EL device enables to emit light with luminousefficiency comparable to that of a conventional material, and isextremely effective in lengthening the lifetime.

INDUSTRIAL APPLICABILITY

In the aromatic amine derivative of the present invention and theorganic EL device using the derivative of the present invention,molecules are hardly crystallized, and the production yield of theorganic EL device is improved. As a result, it becomes possible toprovide an organic EL device having a long lifetime.

1. An organic electroluminescence device comprising an organic thin filmlayer comprising of one or more layers comprising at least a holetransporting layer and a light emitting layer, the organic thin filmlayer being interposed between a cathode and an anode, wherein the holetransporting layer comprises an aromatic amine derivative represented bythe following general formula (1), and the light emitting layercomprises the arylamine compound represented by the following generalformula (B):A-L-B  (1) where: L represents a linking group composed of a substitutedor unsubstituted arylene group having 5 to 50 ring atoms, or a linkinggroup obtained by bonding multiple substituted or unsubstituted arylenegroups each having 5 to 50 ring atoms through a single bond, an oxygenatom, a sulfur atom, a nitrogen atom, or a saturated or unsaturated,divalent aliphatic hydrocarbon group having 1 to 20 ring carbon atoms; Arepresents a diarylamino group represented by the following generalformula (2); and B represents a diarylamino group represented by thefollowing general formula (3) provided that A and B are not identical toeach other:

where Ar₁ to Ar₄ each independently represent a substituted orunsubstituted aryl group having 5 to 50 ring atoms provided that threeor more of Ar₁ to Ar₄ represent aryl groups different from one another:

In the general formula (B), Ar₁₁ to Ar₁₃ each represent an aryl groupwhich has 5 to 40 ring carbon atoms and which may be substituted, and q′represents an integer of 1 to
 4. 2. The organic electroluminescencedevice of claim 1, wherein the light emitting layer further comprisesthe asymmetric anthracene represented by the following general formula(i), (ii) or (iv):

where: Ar represents a substituted or unsubstituted fused aromatic grouphaving 10 to 50 ring carbon atoms; Ar′ represents a substituted orunsubstituted aromatic group having 6 to 50 ring carbon atoms; Xrepresents a substituted or unsubstituted aromatic group having 6 to 50ring carbon atoms, a substituted or unsubstituted aromatic heterocyclicgroup having 5 to 50 ring atoms, a substituted or unsubstituted alkylgroup having 1 to 50 carbon atoms, a substituted or unsubstituted alkoxygroup having 1 to 50 carbon atoms, a substituted or unsubstitutedaralkyl group having 6 to 50 carbon atoms, a substituted orunsubstituted aryloxy group having 5 to 50 ring atoms, a substituted orunsubstituted arylthio group having 5 to 50 ring atoms, a substituted orunsubstituted alkoxycarbonyl group having 1 to 50 carbon atoms, acarboxyl group, a halogen atom, a cyano group, a nitro group, or ahydroxyl group. a, b, and c each represent an integer of 0 to 4; and nrepresents an integer of 1 to
 3. In addition, when n represents 2 ormore, anthracene nuclei in [ ] may be identical to or different fromeach other:

where: Ar¹ and Ar² each independently represent a substituted orunsubstituted aromatic ring group having 6 to 50 ring carbon atoms. mand n each represent an integer of 1 to 4; provided that Ar¹ and Ar² arenot identical to each other when m=n=1 and positions at which Ar¹ andAr² are bound to a benzene ring are bilaterally symmetric, and m and nrepresent different integers when m or n represents an integer of 2 to4; and R¹ to R¹⁰ each independently represent a hydrogen atom, asubstituted or unsubstituted aromatic ring group having 6 to 50 ringcarbon atoms, a substituted or unsubstituted aromatic heterocyclic grouphaving 5 to 50 ring atoms, a substituted or unsubstituted alkyl grouphaving 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkylgroup, a substituted or unsubstituted alkoxy group having 1 to 50 carbonatoms, a substituted or unsubstituted aralkyl group having 6 to 50carbon atoms, a substituted or unsubstituted aryloxy group having 5 to50 ring atoms, a substituted or unsubstituted arylthio group having 5 to50 ring atoms, a substituted or unsubstituted alkoxycarbonyl grouphaving 1 to 50 carbon atoms, a substituted or unsubstituted silyl group,a carboxyl group, a halogen atom, a cyano group, a nitro group, or ahydroxyl group:

where: A¹ and A² each independently represent a substituted orunsubstituted fused aromatic ring group having 10 to 20 ring carbonatoms; Ar¹ and Ar² each independently represent a hydrogen atom, or asubstituted or unsubstituted aromatic ring group having 6 to 50 ringcarbon atoms; R¹ to R¹⁰ each independently represent a hydrogen atom, asubstituted or unsubstituted aromatic ring group having 6 to 50 ringcarbon atoms, a substituted or unsubstituted aromatic heterocyclic grouphaving 5 to 50 ring atoms, a substituted or unsubstituted alkyl grouphaving 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkylgroup, a substituted or unsubstituted alkoxy group having 1 to 50 carbonatoms, a substituted or unsubstituted aralkyl group having 6 to 50carbon atoms, a substituted or unsubstituted aryloxy group having 5 to50 ring atoms, a substituted or unsubstituted arylthio group having 5 to50 ring atoms, a substituted or unsubstituted alkoxycarbonyl grouphaving 1 to 50 carbon atoms, a substituted or unsubstituted silyl group,a carboxyl group, a halogen atom, a cyano group, a nitro group, or ahydroxyl group; and the number of each of Ar¹, Ar², R⁹, and R¹⁰ may betwo or more, and adjacent groups may form a saturated or unsaturatedcyclic structure; provided that the case where groups symmetric withrespect to the X-Y axis shown on central anthracene in the generalformula (iv) bind to 9- and 10-positions of the anthracene does notoccur.
 3. The organic electroluminescence device of claim 1, wherein theAr₃ and Ar₄ in the general formula (3) each independently represent agroup represented by the following general formula (5):

where Ar₆ represents a substituted or unsubstituted aryl group having 5to 50 ring atoms.
 4. The organic electroluminescence device of claim 1,wherein a total number of the ring atoms of the aryl groups representedby Ar₁ to Ar₄ in the general formulae (2) and (3) is 45 to
 72. 5. Theorganic electroluminescence device of claim 1, wherein the aromaticamine derivative is the following compound H1: